Oxalyl chloride → HCID 22287311, compound

Participants

Reaction Steps

To a stirred solution of 2-t-butyldimethylsilyloxy-2-trifluoromethyl-3,3,3-trifluoropropanoic acid, t-butyldimethylsilyl ester (Method 56) (1.05 g) in DCM (10 ml) was added DMF (2 drops) and oxalyl chloride (0.23 ml). The reaction mixture was stirred for 17 hours and was then added to a solution of 2-fluoro-4-(4-methylsulphanylphenylsulphanyl) aniline (Method 6) (0.63 g) in DCM (5 ml) and pyridine (0.22 ml). The reaction mixture was stirred at ambient temperature for 48 hours, evaporated under reduced pressure and the residue purified by chromatography on a silica gel Mega Bond Elut column eluting with 5-20% ethyl acetate/iso-hexane to give the title compound (0.278 g) as a yellow gum. NMR (CDCl3): 0.29 (s, 6H), 0.98 (s, 9H), 2.48 (s, 3H), 6.96-7.0 (m, 1H), 7.06 (d, 1H), 7.2 (d, 2H), 7.31 (d, 2H), 8.23 (t, 1H), 8.62 (brs, 1H).

Provenance & Evidence