Diethyl (2-(4-Phenyl-1H-1,2,3-triazol-1-yl)benzyl) Phosphate
Round 1
Reviewer 1 Report
The research article entitled “Diethyl (2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzyl)phosphate” deals with description and characterization of a typical by-product obtained through the Phospha-Brook rearrangement. Compound 4 is known in the literature (Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands) (2010), 16(3), 461-466) but it is obtained with different reaction and it’s not full characterized (only 1H and 13C NMR). For this reason, the reviewer thinks that the NMR structural characterization using also 2D-NMR is well done and the manuscript is suitable for publication in Molbank because it reflects the aims of the journal.
Author Response
I am enclosing our revised manuscript (molbank-1228843) entitled “Diethyl (2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzyl) phosphate’’ in which we have incorporated the revisions recommended by the reviewers, as noted below. The manuscript was carefully revised and all the reviewer´s comments were all considered. We appreciate their comments, which we believe have improved our manuscript. We would like to thank the reviewers for the careful reading of the manuscript and for all the pertinent suggestions.
The changes made as suggested by the reviewers are given in sequence and are highlighted in the main text (yellow).
Reviewer 2 Report
Authors reported the synthesis of diethyl (2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzyl) phosphate through a Phospha-Brook rearrangement mediated by base. I consider that manuscript meets all requirements to be published in “Molbank” after minor revision. It is important to include four modifications according to the guideline of “Molbank”: (a) the plausible mechanism and its explanation might be included in the manuscript instead of the Supplementary Material, (b) the reporting data of the complete structural characterization for compounds 3 and 4 might be included in the manuscript instead of Supplementary Material, (c) infrared data for compounds 3 and 4 might be taken, and finally (d) MS or HRMS data for compound 4 might be taken. Additional comments are included:
(1) See line 57. in a high yield instead of in a good yield.
(2) See line 79. phosphonate [24], instead of phosphonate,[24]
(3) See Table 1. The numeration of the structure 4 should be completed (i.e. see phenyl ring).
(4) See table 1, numbers 5 and 6. I did not see 13C HMBC. Please, it can be carefully revised.
(5) See table 1, numbers 12 and 12’. I did not see 13C HMBC. Please, it can be carefully revised.
(6) See table 1, numbers 15 and 15’. It might be included in only one file instead of two files because the enantiotopic protons 15 and 15’ would have the same chemical shift. The compound 4 has 15 instead of 16 carbon signals (see Table 1). It does not have a chiral center.
(7) See table 1. In particular, 13C HMBC. C15, C15’ instead of C15.
(8) See line 105. The word “purity” might be modified by “structure”. It is better to use a chromatogram to confirm the purity of compound 4.
(9) See reporting data for compound 4, page S2. The 13C NMR reporting data should have 15 instead of 14 carbon signals (One carbon signal is absent).
Author Response
I am enclosing our revised manuscript (molbank-1228843) entitled “Diethyl (2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzyl) phosphate’’ in which we have incorporated the revisions recommended by the reviewers, as noted below. The manuscript was carefully revised and all the reviewer´s comments were all considered. We appreciate their comments, which we believe have improved our manuscript. We would like to thank the reviewers for the careful reading of the manuscript and for all the pertinent suggestions.
The changes made as suggested by the reviewers are given in sequence and are highlighted in the text (yellow).
Referees: Comments:
Authors reported the synthesis of diethyl (2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzyl) phosphate through a Phospha-Brook rearrangement mediated by base. I consider that manuscript meets all requirements to be published in “Molbank” after minor revision.
- “The plausible mechanism and its explanation might be included in the manuscript instead of the Supplementary Material”.
Answer: We have included the plausible mechanism and its explanation in the main text;
- “The reporting data of the complete structural characterization for compounds 3 and 4 might be included in the manuscript instead of Supplementary Material”
Answer: We have included the reporting data for compounds 3 and 4 in the Section 4.1 of manuscript;
- “Infrared data for compounds 3 and 4 might be taken, and finally”.
Answer: The respective data are already describing in the literature (Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands) (2010), 16(3), 461-466). This reference was added in the main text;
- “MS or HRMS data for compound 4 might be taken”.
Answer: The respective data are already describing in the literature (Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands) (2010), 16(3), 461-466). This reference was added in the main text;
- “See line 57. in a high yield instead of in a good yield”.
Answer: We have changed the word from ‘‘good’’ to ‘‘high’’ in the manuscript;
- “See line 79. phosphonate [24], instead of phosphonate,[24]”
Answer: We have changed the reference quote to before the comma;
- “See Table 1. The numeration of the structure 4 should be completed (i.e. see phenyl ring).”
Answer: We have completed the numeration of the structure 4 on the Table 1;
- “See table 1, numbers 5 and 6. I did not see 13C HMBC. Please, it can be carefully revised”.
Answer: We have reviewed and added the 13C HMBC of the numbers 5 and 6 on the Table 1;
- “See table 1, numbers 12 and 12’. I did not see 13C HMBC. Please, it can be carefully revised”.
Answer: We have reviewed and added the 13C HMBC of the numbers 12 and 12’ on the Table 1;
- “See table 1, numbers 15 and 15’. It might be included in only one file instead of two files because the enantiotopic protons 15 and 15’ would have the same chemical shift. The compound 4 has 15 instead of 16 carbon signals (see Table 1). It does not have a chiral center”.
Answer: We have removed line 15' from Table 1 and adjusted the spectral data of compound 4 in Section 4.1;
- “See table 1. In particular, 13C HMBC. C15, C15’ instead of C15”.
Answer: We have changed the C 15 by C15, C15’ in the line 14 column of 13C HMBC on the Table 1;
- “See line 105. The word “purity” might be modified by “structure”. It is better to use a chromatogram to confirm the purity of compound 4.”
Answer: We have changed the word from “purity” to “structure” in the main text;
- “See reporting data for compound 4, page S2. The 13C NMR reporting data should have 15 instead of 14 carbon signals (One carbon signal is absent)”.
Answer: We have reviewed and it was verified that the missing signal is overlap on the 130.2 ppm signal.
Best regards,
Prof. M.S. Silva
In name of all authors
Author Response File: 
Author Response.pdf
