Ammonium Chloride → 1-(3-broMo-5-fluorophenyl)ethanol

To a solution of 3-bromo-5-fluorobenzaldehyde (6.0 g, 29.6 mmol, prepared according to patent WO 0066556) in THF (100 ml) was added dropwise at 0° C. methylmagnesiumchloride (3N in THF, 12 ml). The reaction mixture was stirred for 3 hours at room temperature and then sat. NH4Cl solution was added. The aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with water, dried over MgSO4, filtered and the solvent was removed in vacuo. The crude product was purified by chromatography over silica gel to yield 1-(3-bromo-5-fluoro-phenyl)-ethanol (2.9 g, 45%), 1H-NMR (300 MHz, CDCl3): δ=7.31 (s, 1H), 7.14 (d, 1H), 7.04 (d, 1H), 4.82-4.94 (m, 1H), 1.51 (d, 3H).

1. extractionThe aqueous phase was extracted twice with ethyl acetate
2. washThe combined organic layers were washed with water
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. customthe solvent was removed in vacuo
6. customThe crude product was purified by chromatography over silica gel

ORD record

ord-6635c2661e0f4b198679c1388db2defd

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07005432B2