2,3,6-Trichlorobenzaldehyde → 1-(2,3,6-Trichlorophenyl)ethanol

General Procedure CC: To a solution of 2,3,6-trichlorobenzaldehyde (1.00 g, 4.77 mmol) in THF (10 mL) was added MeMgBr/butyl ether (1M, 5.72 mL, 5.72 mmol) at 0° C. under nitrogen, the resulting mixture was allowed to warm to rt and stirred overnight. The mixture was quenched with sat. aq. NH4Cl (15 mL) at 0° C., then diluted with Et2O (15 mL), the organic phase was washed with brine (20 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The material was purified by silica gel chromatography using Hexane/EtOAc (80:20) as eluent to give the desired product as a colorless oil. 1H NMR (CDCl3, 400 MHz): δ=1.69 (d, J=6.8 Hz, 3H), 2.97 (br. s., 1H), 5.67 (q, J=6.8 Hz, 1H), 7.30 (d, J=3.0 Hz, 1H), 7.35-7.38 (m, 1H).

1. customThe mixture was quenched with sat. aq. NH4Cl (15 mL) at 0° C.
2. additiondiluted with Et2O (15 mL)
3. washthe organic phase was washed with brine (20 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customThe material was purified by silica gel chromatography

ORD record

ord-604bde503c40499c800712c1bec43dee

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022206B2