Tert-Butylamine → 2-Bromo-5-phenoxyphenol

Participants

Reaction Conditions

Reaction Steps

To a solution of t-butylamine (1.1 ml, 10.7 mmol) in 13 ml toluene, cooled to -30° C. was added bromine (0.28 ml, 5.35 mmol). The mixture was cooled to -70° C. and was treated with 3-phenoxyphenol (2.0 g, 10.7 mmol) dissolved in 2 ml CH2Cl2. The reaction was stirred to ambient temperature over 5 h, quenched with water and diluted with CH2Cl2. The organic phase was washed with water and brine and dried over Na2SO4. Column chromatography (SiO2 ; 5:95 EtOAc/Hex) afforded 380 mg (14%) of 2-bromo-5-phenoxyphenol.

Provenance & Evidence