Hydrochloric Acid → HCID 12097219, compound

8.63 g (0.05 mole) of 2-chloro-4'-fluoroacetophenone were dissolved in 60 ml of diethyl ether. The solution was stirred under a stream of nitrogen, and 200 ml (0.057 mole) of a diethyl ether solution of trimethylsilylmethylmagnesium chloride were added dropwise at such a rate that the temperature of the reaction mixture did not rise above 15° C.-20° C. The reaction mixture was then stirred for a further 1 hour at room temperature, after which it was poured into 200 ml of ice water, and its pH was adjusted to a value of 6-7 by the addition of 5% w/v aqueous hydrochloric acid. It was then extracted with 100 ml of ethyl acetate. The organic extract was washed twice, each time with 50 ml of a saturated aqueous solution of sodium chloride It was then dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure, to afford a crude oily product. This crude oily product was purified by silica gel column chromatography, using mixtures of ethyl acetate and hexane ranging from 1:10 to 1:5 by volume, to give 8.8 g (yield 67.7%) of the title compound as an oily substance.

1. additionwere added dropwise at such a rate that the temperature of the reaction mixture
2. customdid not rise above 15° C.-20° C
3. additionwas adjusted to a value of 6-7 by the addition of 5%
4. extractionIt was then extracted with 100 ml of ethyl acetate
5. extractionThe organic extract
6. washwas washed twice
7. dry with materialeach time with 50 ml of a saturated aqueous solution of sodium chloride It was then dried over anhydrous sodium sulfate
8. customthe solvent was removed by distillation under reduced pressure
9. customto afford a crude oily product
10. customThis crude oily product was purified by silica gel column chromatography

ORD record

ord-0746a5345041433a8ae27610ef50f37a

Source dataset

uspto-grants-1994_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05306712