[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].C(N(CC)CC)C.[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:16]=1[CH:17]=O.O>CS(C)=O>[Cl:14][C:15]1[C:16]2[CH:17]=[C:2]([C:1]([O:5][CH3:6])=[O:4])[S:3][C:19]=2[CH:20]=[CH:21][CH:22]=1Methyl thioglycolate (11.3 ml) was added under nitrogen to a stirred solution of triethylamine (45 ml) in dimethyl sulphoxide (160 ml), then the mixture was stirred at ambient temperature for 30 minutes. A solution of 2-chloro-6-fluorobenzaldehyde (20 g) in dimethyl sulphoxide (80 ml) was added then the mixture was stirred at 95° C. for 4.66 hours, allowed to stand at ambient temperature for 18 hours and poured into water (1600 ml). The resulting solid was collected by filtration, washed with water (3×100 ml), and dried in vacuo to give methyl 4-chlorobenzo[b]thiophene-2-carboxylate (22.4 g) as an off-white solid, m.p. 84-86° C.
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