Dimethyl Sulfoxide → (3-trifluoromethyl-phenoxy)-acetaldehyde

Temperature

-78 °C

A cooled (−78° C.) solution of oxalyl chloride (0.49 ml; 5.821 mmol) in anhydrous DCM (25 ml) was treated dropwise with a solution of dimethyl sulfoxide (0.91 ml; 11.641 mmol) in anhydrous DCM (4 ml). After 10 min., a solution of 2-(3-trifluoromethyl-phenoxy)-ethanol (0.800 g; 3.880 mmol) in DCM (8 ml) was added dropwise, and the reaction mixture was further stirred at −78° C. for 30 min. TEA (2.70 ml; 19.402 mmol) was then added dropwise, and after 10 min. the resulting mixture was allowed to warm-up to 0° C. before a mixture of water (2.5 ml) and DCM (25 ml) was added. The aq. layer was extracted with DCM (2×25 ml), and the mixed organic layers were then washed with aq. sat. NaHCO3 (20 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure to give (3-trifluoromethyl-phenoxy)-acetaldehyde as a yellow oil (0.792 g; 99%). This aldehyde was used for the next step without additional purification.

1. waitafter 10 min. the resulting mixture was allowed
2. additionwas added
3. extractionThe aq. layer was extracted with DCM (2×25 ml)
4. washthe mixed organic layers were then washed with aq. sat. NaHCO3 (20 ml)
5. dry with materialdried over anh. MgSO4
6. filtrationfiltered
7. concentrationconcentrated to dryness under reduced pressure

ORD record

ord-b54531deb57944269f4728149f3452a6

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188082B2