Phosphorus tribromide → 1-Bromo-4-(1-bromoethyl)benzene

A solution of 1-(4-bromophenyl)ethanol (1.492 mmol) in dichloromethane (8 mL) at 0° C. was treated dropwise with a solution of phosphorous tribromide (0.597 mmol) in dichloromethane (2 mL). The reaction was allowed to warm to room temperature and was stirred overnight. The reaction was then quenched with saturated aq sodium bicarbonate (10 mL) and was stirred for 2 h. The biphasic mixture was further diluted with dichloromethane (50 mL) and the organic layer was separated from the aqueous layer. The organic layer was dried over sodium sulfate, filtered and concentrated to dryness in vacuo. Purification of the residue by flash chromatography (0-25% ethyl acetate/hexanes) gave the title product (91 mg, 23% yield) as a clear oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.97 (d, J=6.82 Hz, 3 H) 5.50 (q, J=6.82 Hz, 1 H) 7.48 (d, J=8.59 Hz, 2 H) 7.57 (m, J=8.59 Hz, 2 H).

1. customThe reaction was then quenched with saturated aq sodium bicarbonate (10 mL)
2. stirringwas stirred for 2 h
3. additionThe biphasic mixture was further diluted with dichloromethane (50 mL)
4. customthe organic layer was separated from the aqueous layer
5. dry with materialThe organic layer was dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated to dryness in vacuo
8. customPurification of the residue by flash chromatography (0-25% ethyl acetate/hexanes)

ORD-Eintrag

ord-489d8f1c6fca4f1cb75ca8e42e50fe4c

Quelldatensatz

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09084794B2