2-Chlorobenzaldehyde → 1-Chloro-2-(2-methoxyvinyl)benzene

To a stirred solution of (methoxymethyl)triphenylphosphonium chloride (10 g, 28 mmol) in tetrahydrofuran (46 mL) cooled at −15° C. was added potassium tert-butoxide (3.7 g, 31 mmol) as a solid in one portion. After 5 minutes, 2-chlorobenzaldehyde (2.0 g, 14 mmol) was added, and the reaction mixture was warmed to room temperature and stirred for two hours. The reaction was quenched with saturated aqueous ammonium chloride solution (5 mL), tetrahydrofuran evaporated in vacuo, and the resulting residue was diluted with diethyl ether (100 mL) and water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 80 g, ISCO, 0-10% ethyl acetate in heptane) to afford the title compound as a colorless oil (2.4 g, 100%), which was used in the next step without further purification.

1. customThe reaction was quenched with saturated aqueous ammonium chloride solution (5 mL), tetrahydrofuran
2. customevaporated in vacuo
3. additionthe resulting residue was diluted with diethyl ether (100 mL) and water (100 mL)
4. customThe organic layer was separated
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated in vacuo
8. customto afford a residue that
9. customwas purified by flash chromatography (silica, 80 g, ISCO, 0-10% ethyl acetate in heptane)

ORD record

ord-46ad1198f94e46db99a9b9903368fe9a

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206175B2