Ammonium Chloride → 4-Bromo-beta,beta-dimethylbenzeneethanol

To a solution of 2-(4-bromophenyl)-2-methylpropanoate (8.9 g, 33 mmol) in tetrahydrofuran (100 mL) under nitrogen was added LiAlH4 (1.6 g, 43 mmol) in portions at 0° C. The resulting solution was stirred at 0° C. for 1 hour before the addition of saturated aqueous NH4Cl solution (50 mL). The mixture was then extracted with ethyl acetate (3×80 mL). All the organic solution was dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography with 2-5% ethyl acetate in hexane to afford the title compound as a colorless oil. MS ESI: [M+H]+ m/z 229, 231; 1H NMR (400 MHz, CDCl3) δ 7.47 (d, J=6.8 Hz, 2H), 7.28 (d, J=6.8 Hz, 2H), 3.61 (s, 2H), 1.58 (s, 6H).

1. extractionThe mixture was then extracted with ethyl acetate (3×80 mL)
2. dry with materialAll the organic solution was dried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe crude residue was purified by flash column chromatography with 2-5% ethyl acetate in hexane

ORD record

ord-9b1eef2d7f8b4aee92223f7ac0f5aaba

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394282B2