4-tert-Butylphenol → 4-tert-Butyl-2-chlorophenol

Participants

Reaction Steps

1.50 g (10 mmol) of 4-tert.-butyl phenol were dissolved in 40 ml acetonitrile. 1.34 g (10 mmol) of NCS were added and the reaction mixture was stirred at rt over night. The reaction mixture was heated for 1.5 h to reflux. Then additional 134 mg (1 mmol) of NCS were added and the reaction mixture was heated to reflux for 2 h. The solvent was evaporated and the residue was stirred with diethyl ether for 15 min. The solid was filtered off and the filtrate was evaporated. The residue was purified by column chromatography (100 silica gel, DCM) to yield 1.49 g (81%) of 4-tert.-butyl-2-chloro-phenol as a colorless viscous oil. 1H NMR (DMSO-d6, 300 MHz): δ 9.85 (s, 1H), 7.26 (s, 1H), 7.14 (d, 2H), 6.88 (d, 2H), 1.22 (s, 9H).

Provenance & Evidence