Practical Synthesis of 4‐Fluoro‐2‐(methylthio)benzylamine and the Corresponding Sulfone and Sulfonamide
1
a Merck Research Laboratories, Department of Medicinal Chemistry , West Point, Pennsylvania, USA
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Publication type: Journal Article
Publication date: 2007-06-01
scimago Q3
wos Q3
SJR: 0.322
CiteScore: 4.3
Impact factor: 1.8
ISSN: 00397911, 15322432
Organic Chemistry
Abstract
Practical syntheses of 4‐fluoro‐2‐(methylthio)benzylamine 1 and the corresponding 2‐methylsulfonyl analog 2 are reported. The methylthio moiety was introduced regioselectively by two methods. In the first method, metallation of 4‐fluoro‐2‐bromobenzoic acid, followed by treatment with dimethyl disulfide resulted in an easily isolated intermediate, which was suitable for further elaboration to the benzylamine 1. In the second method, selective nucleophilic aromatic substitution of 2,4‐difluorobenzonitrile with methanethiolate was explored, and a mechanistic rationale was offered for solvent effects on regioselectivity. Optimized conditions furnished the key 4‐fluoro‐2‐(methylthio)benzonitrile for further functionalization to the 2‐methylsulfonyl‐4‐fluorobenzylamine 2. In addition, the analogous sulfonamide 3 was prepared in a straightforward manner from 5‐fluoro‐2‐methylbenzenesulfonyl chloride.
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PERLOW D. S. et al. Practical Synthesis of 4‐Fluoro‐2‐(methylthio)benzylamine and the Corresponding Sulfone and Sulfonamide // Synthetic Communications. 2007. Vol. 37. No. 11. pp. 1887-1897.
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PERLOW D. S., Kuo M. S., Moritz H. M., Wai J. S., Egbertson M. S. Practical Synthesis of 4‐Fluoro‐2‐(methylthio)benzylamine and the Corresponding Sulfone and Sulfonamide // Synthetic Communications. 2007. Vol. 37. No. 11. pp. 1887-1897.
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TY - JOUR
DO - 10.1080/00397910701319221
UR - https://doi.org/10.1080/00397910701319221
TI - Practical Synthesis of 4‐Fluoro‐2‐(methylthio)benzylamine and the Corresponding Sulfone and Sulfonamide
T2 - Synthetic Communications
AU - PERLOW, DEBRA S.
AU - Kuo, Michelle S
AU - Moritz, H Marie
AU - Wai, John S.
AU - Egbertson, Melissa S
PY - 2007
DA - 2007/06/01
PB - Taylor & Francis
SP - 1887-1897
IS - 11
VL - 37
SN - 0039-7911
SN - 1532-2432
ER -
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@article{2007_PERLOW,
author = {DEBRA S. PERLOW and Michelle S Kuo and H Marie Moritz and John S. Wai and Melissa S Egbertson},
title = {Practical Synthesis of 4‐Fluoro‐2‐(methylthio)benzylamine and the Corresponding Sulfone and Sulfonamide},
journal = {Synthetic Communications},
year = {2007},
volume = {37},
publisher = {Taylor & Francis},
month = {jun},
url = {https://doi.org/10.1080/00397910701319221},
number = {11},
pages = {1887--1897},
doi = {10.1080/00397910701319221}
}
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MLA
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PERLOW, DEBRA S., et al. “Practical Synthesis of 4‐Fluoro‐2‐(methylthio)benzylamine and the Corresponding Sulfone and Sulfonamide.” Synthetic Communications, vol. 37, no. 11, Jun. 2007, pp. 1887-1897. https://doi.org/10.1080/00397910701319221.