Hydrochloric Acid → Ethyl 4-benzylthio-3-nitrobenzoate

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Reaction Steps

Ethyl 4-chloro-3-nitrobenzoate (10 g) and benzyl mercaptan (5.41 g) were dissolved in N,N-dimethylformamide and whilst stirring, lithium hydroxide monohydrate (1.83 g) was added. The mixture was stirred overnight then poured into ether and 2N hydrochloric acid. The organic phase was washed with water, dried over anhydrous magnesium sulphate and evaporated to yield ethyl 4-benzylthio-3-nitrobenzoate (10.16 g), obtained as an oil, NMR (CDCl3) δ1.41 (3H, t), 4.24 (2H,s), 4.40 (2H,q), 7.3-7.47 (5H), 7.53 (1H,d), 8.14 (1H,dd), 8.86 (1H,d).

Provenance & Evidence