Potassium Bromide → [2-(2,2,2-Trifluoroethoxy)-phenoxy]-acetaldehyde

Participants

Reaction Conditions

Reaction Steps

2-[2-(2,2,2-Trifluoro-ethoxy)-phenoxy]-ethanol (XIV) (6 g, 0.025 moles) was added to dichloromethane (60 ml). To this solution sodium bicarbonate (1.2 g, in 10 ml water) was added. Reaction mixture was cooled to 0° C. and potassium bromide (0.24 g in 1 ml of water) and TEMPO (2,2,6,6-Tetramethylpiperidine-1-oxyl) (0.02 g, 0.13 mmole) were added in single lot. To this reaction mixture sodium hypochlorite solution (45 ml of 12.5% w/v) was added over a period of 15 minutes at 0-5° C. Continued stirring of reaction mass at 0-5°. After completion of reaction, organic layer was separated. The aqueous layer was extracted with dichloromethane. Combined organic layer was washed with 10% aqueous sodium hydroxide solution, followed by brine. The organic layer was dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane (5/95) as eluent to give 0.40 g of (VIII) as colourless solid, melting at 57-58° C.

Provenance & Evidence