Methyl iodide → Carbanilic acid, p-bromodithio-, methyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of carbon disulfide (6 mL, 100 mmol) at 0 ° C. under a nitrogen atmosphere was added a mixture of p-bromoaniline (1.72 g, 10 mmol) and triethylamine (1.4 mL, 10 mmol) dropwise via an addition funnel. The reaction mixture was stirred at 0 ° C. for 1.5 h, and then allowed to warm to room temperature overnight. To the reaction mixture was added iodomethane (0.62 mL, 10 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with diethyl ether (40 mL), and the resulting precipitate was filtered off. The filtrate was concentrated under reduced pressure and trituration of the residue with hexane afforded the title compound of Step E (2.34 g) as a solid melting at 111-112 ° C. 300 MHz 1H NMR (CDCl3): δ 8.67 (s,1H), 7.53 (d,2H), 7.38 (d,2H), 2.67 (s,3H).

Provenance & Evidence