ChemicalBook CAS DataBase List 1-Naphthalenesulfonyl fluoride

1-Naphthalenesulfonyl fluoride synthesis

10synthesis methods

Product Name:1-Naphthalenesulfonyl fluoride
CAS Number:317-55-5
Molecular formula:C10H7FO2S
Molecular Weight:210.22

85-46-1
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Yield:317-55-5 97%

Reaction Conditions:

with potassium hydrogen difluoride;tetra-n-butyl-ammonium chloride in dichloromethane;lithium hydroxide monohydrate at 20; for 48 h;

Steps:

Sulfonyl Fluorides 1d, 1e, and 1f; General Procedure

General procedure: A 50 mL round-bottomed flask was charged with an aq solution ofKHF2 (3.12 g in 8.04 g of H2O; ca. 28% w/w; 40.0 mmol), the respectivearenesulfonyl chloride (20.0 mmol), Bu4NCl (0.056 g, 0.20 mmol, 1mol%), and DCM (22 mL), and the reaction mixture was stirred vigorouslyat r.t. for 4 h (1d) and 48 h (1e and 1f). Then, the mixture wastransferred to a separatory funnel, extracted with DCM (3 × 50 mL),and the combined organic phases were dried (MgSO4). The mixturewas filtered through a pad of silica gel (d = 4 cm; ? 6 cm), rinsed withDCM (500 mL), and the combined filtrates were evaporated, and driedin vacuo to obtain the desired sulfonyl fluoride. The products 1d, 1e,and 1f were analytically pure.

References:

Talko, Alicja;Antoniak, Damian;Barbasiewicz, Micha? [Synthesis,2019,vol. 51,# 11,p. 2278 - 2286]