3-Hydroxybenzenesulfonyl Chloride synthesis

Yield: 76%

Reaction Conditions:

with thionyl chloride in N,N-dimethyl-formamide at 60; for 5 h;

Steps:

1.1 Step 1 3-Hydroxyphenyl-1-sulfonyl chloride
Step 1
3-Hydroxyphenyl-1-sulfonyl chloride
3-Hydroxybenzenesulfonic acid 1a (5.6 g, 0.03 mol, prepared by a known method disclosed in "") was dissolved in 60 mL of thionyl chloride, followed by addition of 0.25 mL of N, N-dimethylformamide.
The reaction solution was uniformly stirred, and then heated up to 60°C and reacted for 5 h.
The reaction solution was concentrated under reduced pressure.
100 mL of water was added to the resulting residue, and the reaction solution was extracted with ethyl acetate (100 mL*3).
The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure.
The resulting residue was purified by silica gel column chromatography with elution system C to obtain the title product 3-hydroxyphenyl-1-sulfonyl chloride 1b (1.6g, a light red oil) in 76% yield.

References:

Jiangsu Hansoh Pharmaceutical Co., Ltd.;LAN, Jiong;SUN, Piaoyang;CHEN, Lei;PENG, Wei;LIU, Xing;DONG, Qing EP2921479, 2015, A1 Location in patent:Paragraph 0093; 0094