A Publication of Reliable Methods for the Preparation of Organic
Compounds Annual Volume Org. Synth. 1995, 72, 209 DOI:
10.15227/orgsyn.072.0209 [Benzene, [(fluoromethyl)sulfonyl]-]
Submitted by James R. McCarthy, Donald P. Matthews, and John P.
Paolini1. Checked by Carmen M. Simone and Albert I. Meyers. 1.
Procedure CAUTION! All reactions should be conducted in an
efficient fume hood. A. Fluoromethyl phenyl sulfide (1). To a
1-L, three-necked, round-bottomed flask, equipped with a
magnetic stirring bar, air condenser and thermometer are added
methyl phenyl sulfoxide (25.2 g, 0.18 mol) (Note 1) and
chloroform (150 mL) (Note 2). The flask is placed in a cooling
bath containing 3 L of water kept at 20°C (Note 3).
Diethylaminosulfur trifluoride (DAST) (38.5 g, 31.6 mL, 0.24
mol) (Note 4) is added to the flask, followed by antimony
trichloride (0.50 g, 0.0022 mol) (Note 5), and an additional 50
mL of chloroform. The light yellow reaction mixture is stirred
under an argon atmosphere. After 2 to 8 hr, an exothermic