2,6-Dichlorobenzaldehyde → HCID 12105278, compound

To a solution of 2,6-dichlorobenzaldehyde (880 mg, 5.03 mmol) in THF (10 mL) was added EtMgCl/THF (2.0 M, 3 mL, 6.0 mmol) at 0° C. under nitrogen, the resulting mixture was allowed to warm to rt and stirred at rt overnight. The mixture was quenched with sat. aq. NH4Cl (5 mL) at 0° C., then diluted with Et2O (50 mL), the organic phase was washed with brine (20 mL), and dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography (Hex:EtOAc=80:20) to give the title compound as a colorless oil. 1H NMR (CDCl3): δ=1.00 (t, J=7.4 Hz, 3H), 1.95-2.11 (m, 2H), 2.82 (d, J=10.4 Hz, 1H, —OH), 5.34 (m, 1H), 7.13 (t, J=7.6 Hz, 1H), 7.29 (d, J=7.8 Hz, 2H.)

1. customThe mixture was quenched with sat. aq. NH4Cl (5 mL) at 0° C.
2. additiondiluted with Et2O (50 mL)
3. washthe organic phase was washed with brine (20 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. customThe residue was purified by silica gel chromatography (Hex:EtOAc=80:20)

ORD record

ord-cf42c01043ef41b59cbf4a8634ddf792

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022206B2