3-Chlorobenzotrifluoride → 2-Chloro-6-(trifluoromethyl)benzaldehyde

To a solution of 1-chloro-3-trifluoromethylbenzene (1.0 g, 5.54 mmol) in THF (15 mL) cooled to −78° C., under N2 protection was added dropwise n-BuLi (3.81 mL of a 1.6 M solution in hexane, 6.1 mmol). After an hour, formic acid methyl ester (664.8 mg, 11.08 mmol) was added slowly to the solution. After the addition, the solution was warmed to ambient temperature slowly and stirred for 30 min. The reaction mixture was quenched with water and the aqueous layer was extracted with EtOAc. The organic layer was washed with water, brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (15:1) as eluent to give 2-chloro-6-trifluoromethylbenzaldehyde as a colorless oil.

1. waitAfter an hour
2. additionAfter the addition
3. customThe reaction mixture was quenched with water
4. extractionthe aqueous layer was extracted with EtOAc
5. washThe organic layer was washed with water, brine
6. dry with materialdried with MgSO4
7. filtrationfiltered
8. customThe solvent was removed under reduced pressure
9. customthe residue was purified by flash chromatography

ORD record

ord-ecdac2f096c449f8933712c7b067454a

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222248B2