Carbon Tetrachloride → 2-Bromo-4-tert-butylphenol

A solution of bromine (7.18 mL, 0.14 mol) in chloroform (25 mL) was added dropwise over 2 hours to a solution of 4-tert-butyl-phenol (20 g, 0.133 mol) in 1:1 v/v chloroform:carbon tetrachloride (64 mL) at 0° C. under nitrogen until a slight red coloration persisted (approximately 1 mL of bromine solution remained). The reaction mixture was then purged with nitrogen overnight. The resulting tan solution was diluted with dichloromethane (50 mL), washed with 1% aqueous sodium thiosulfate solution (100 mL) and saturated brine (100 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give 2-bromo-4-(tert-butyl)phenol (30.5 g, quantitative yield) as a colorless oil.

1. customat 0° C.
2. customThe reaction mixture was then purged with nitrogen overnight
3. additionThe resulting tan solution was diluted with dichloromethane (50 mL)
4. washwashed with 1% aqueous sodium thiosulfate solution (100 mL) and saturated brine (100 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-75d1d3c8a0a1470cbca3ca6679537dae

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409893B2