Water → (5-Bromopentyl)benzene

Phosphorus tribromide (4.7 ml, 49.8 mmol) was added dropwise to a solution of 5-phenylpentan-1-ol (3 ml, 17.8 mmol) in dioxane (70 ml). The reaction mixture was stirred for 2 hours at room temperature. Another portion of phosphorus tribromide (4.7 m. 49.8 mmol) was added. The reaction mixture was stirred for 16 h at room temprature. It was cooled to 0° C. Water (60 ml) was added dropwise. The reaction mixture was diluted with ethyl acetate (100 ml). The phases were separated. 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 sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (50 g), using ethyl acetate/heptane (1:10) as eluent, to give 1.35 g of 1-bromo-5-phenylpentane.

1. stirringThe reaction mixture was stirred for 16 h at room temprature
2. temperatureIt was cooled to 0° C
3. customThe phases were separated
4. extractionThe aqueous phase was extracted with ethyl acetate (2×100 ml)
5. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml)
6. dry with materialdried over magnesium sulfate
7. customThe solvent was removed in vacuo
8. customThe crude product was purified by flash chromatography on silica (50 g)

ORD record

ord-bc7972ff90b545cba67eccff77153a1f

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610721B2