Phosphorus tribromide → (4-(Bromomethyl)-2-ethoxyphenoxy)(tert-butyl)dimethylsilane

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-(tert-butyldimethylsilyloxy)-3-ethoxyphenyl)methanol (12.5 g, 44.4 mmol, 1.0 equiv.) in CH2CI2 (45 mL), PBr3 (5.0 mL, 53.2 mmol, 1.2 equiv.) was added at 0° C., and the mixture was stirred at 0° C. for 30 min. After slow addition of sat. aq. NaHCO3-solution, the aqueous layer was extracted with CH2Cl2 (2×). The combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated to yield 14.5 g (94%) of (4-(bromomethyl)-2-ethoxyphenoxy)(tert-butyl)dimethylsilane as a light yellow oil.

Provenance & Evidence