Acetaldehyde → HCID 57812530, compound

Temperature

-78 °C

To a solution of LDA (6 mL, 12 mmol) in THF (10 mL) was added 3-chlorobromobenzene (1.91 g, 9.98 mmol) in THF (5 mL) at −78° C. under nitrogen, the resulting mixture was stirred at −78° C. for 1 h, then a solution of acetaldehyde (0.66 g, 15 mmol) in THF (5 mL) was added. The mixture was slowly warmed to rt. The mixture was quenched with water (10 mL), and diluted with EtOAc (50 mL). The organic phase was separated, washed with brine (10 mL), and dried over anhydrous sodium sulfate. The crude material was purified by silica gel chromatography (Hex:EtOAc=95:5→90:10) to give the title compound as a colorless oil. 1H NMR (CDCl3): δ=1.64 (d, J=6.8 Hz, 3H), 2.98 (d, J=10.4 Hz, 1H, —OH), 5.58 (m, 1H), 7.04 (t, J=8.1 Hz, 1H), 7.31 (dd, J=8.1, 1.2 Hz, 1H), 7.49 (dd, J=8.1, 1.0 Hz, 1H).

1. temperatureThe mixture was slowly warmed to rt
2. customThe mixture was quenched with water (10 mL)
3. additiondiluted with EtOAc (50 mL)
4. customThe organic phase was separated
5. washwashed with brine (10 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. customThe crude material was purified by silica gel chromatography (Hex:EtOAc=95:5→90:10)

ORD record

ord-1cba05c0f86542abb81b05522d5ea890

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022206B2