Methanol → 1-Chloro-4-methoxy-2-methyl-5-nitrobenzene

Participants

Reaction Steps

A solution of (trimethylsilyl)diazomethane (2.0 M in hexane, 13.3 mL, 26.6 mmol) was added to a mixture of 4-chloro-5-methyl-2-nitro-phenol (1.0 g, 5.33 mmol) and diisopropylethylamine (1.04 mL, 6.13 mmol) in a mixture of anhydrous methanol and anhydrous acetonitrile (1/1, 50 mL) and the reaction mixture was stirred for 1 hour. Glacial acetic acid (5 drops) was then added and the resulting mixture was evaporated under reduced pressure. The residue was partitioned between diethyl ether (100 mL) and water (50 mL); the organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 1.07 g of 1-chloro-4-methoxy-2-methyl-5-nitro-benzene as a light orange solid without further purifications.

Provenance & Evidence