Cyclopropanecarboxylic acid, 1-[4-(chlorosulfonyl)phenyl]-, methyl ester synthesis

Yield: 57%

Reaction Conditions:

with chlorosulfonic acid

Steps:

36.2 Step 2.
Step 2. Preparation of 1-(4-Chlorosulfonyl-phenyl)-cyclopropanecarboxylic acid methyl ester (Compound 36B) Chlorosulfonic acid (10 mL) was cooled to 0° C. Then compound 36A (6.80 g, 38.6 mmol) was added over 30 min. The mixture was stirred at RT for 3 h and was poured into ice (~500 g). The cloudy solution was extracted with ether (2*200 mL). The extracts were dried with magnesium sulfate and concentrated to give a brown oil which was passed through a short pad of silica gel to afford the desired product 36B (6.05 g, 57%) as white plates. MS: 239 (M-Cl)⁺.

References:

Bratton, Larry D.;Cheng, Xue-Min;Erasga, Noe;Filzen, Gary F.;Geyer, Andrew G.;Lee, Chitase;Trivedi, Bharat K.;Unangst, Paul C. US2004/209936, 2004, A1