Water → 1-Bromo-4-phenylbutane

Phosphorus tribromide (17.6 ml, 186 mmol) was added dropwise to a solution of 4-phenyl-1-butanol (10.0 g, 66.6 mmol) in dioxane (200 ml). The reaction mixture was stirred for 1 hour at room temperature. Another portion of phosphorus tribromide (17.6 ml, 186 mmol) was added dropwise. The reaction mixture was stirred for 16 hours at room temperature. It was cooled to 0° C. Water (130 ml) was added dropwise. The reaction mixture was stirred for 30 min at room temperature. It was diluted with ethyl acetate (200 ml) and washed with 1 N hydrochloric acid (200 ml). The aqueous phase was extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (300 g), using ethyl acetate/heptane 1:3 as eluent, to give 8.54 g of (4-bromobutyl)benzene.

1. stirringThe reaction mixture was stirred for 16 hours at room temperature
2. temperatureIt was cooled to 0° C
3. stirringThe reaction mixture was stirred for 30 min at room temperature
4. washwashed with 1 N hydrochloric acid (200 ml)
5. extractionThe aqueous phase was extracted with ethyl acetate (2×100 ml)
6. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml)
7. dry with materialdried over magnesium sulphate
8. customThe solvent was removed in vacuo
9. customThe crude product was purified by flash chromatography on silica (300 g)

ORD record

ord-deb46993fb114e139e3bc545b548160c

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610721B2