3-Chloro-2-fluorobenzaldehyde → HCID 86721095, compound

Temperature

0 °C

A solution of 3-chloro-2-fluorobenzaldehyde (2.36 g, 14.88 mmol) in THF (29.8 mL) was cooled down to −78° C. under argon. To the solution was added vinyl magnesium bromide (1 M in THF) (20 mL, 20.00 mmol) via syringe pump over 30 min, while stirring was continued at −78° C. After 2 h, the reaction mixture was warmed to 0° C., quenched with 1 N HCl and adjusted the pH to 4. The aqueous layer was extracted with EtOAc (2×), and the combined organic layers were washed with brine and dried over MgSO4. The solids were filtered off and the filtrate was concentrated under vacuum to yield a yellow oil as the desired product. MS (ESI) m/z: 169.1 (M+H-H2O)+.

1. customwas continued at −78° C
2. customquenched with 1 N HCl
3. extractionThe aqueous layer was extracted with EtOAc (2×)
4. washthe combined organic layers were washed with brine
5. dry with materialdried over MgSO4
6. filtrationThe solids were filtered off
7. concentrationthe filtrate was concentrated under vacuum

ORD record

ord-037abc8732824fefa8e674a6a07ee73c

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901115B2