Benzenepropanal, 4-fluoro-α,α-dimethyl- synthesis

5synthesis methods

Product Name:Benzenepropanal, 4-fluoro-α,α-dimethyl-
CAS Number:4092-92-6
Molecular formula:C11H13FO
Molecular Weight:180.22

483368-32-7
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4092-92-6
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Yield:-

Reaction Conditions:

Stage #1: 2,2-dimethyl-3-(4-fluoro)phenylpropanolwith oxalyl dichloride;dimethyl sulfoxide in dichloromethane at -70 - -50; for 1.5 h;
Stage #2: with triethylamine in dichloromethane at -50 - 0; for 1.41667 h;

Steps:

25a.c

To a stirred solution of oxalyl chloride (1.06 mL, 1.6 equiv. ) in 28 mL of anhydrousCH2Cl2 at-65 C was added DMSO (1.72 mL, 1.72 equiv. ) drop wise over a period of 10 minutes. The mixture was stirred for 20 minutes at-65--60 C. Then a solution of 2,2-dimethyl-3- (4- fluoro) phenylpropanol (1.38 g) in 18 mL of anhydrousCH2C12 was added drop wise over a period of 20 minutes at- 70--60 C. After stirring for 40 minutes at-60-50 C triethylamine (3.43 mL, 3.25 equiv. ) was added drop wise over a period of 10 minutes, and the mixture was continued to stir for 1.25 hrsat-50-0 C. Then 100 mL of diethyl ether was added and the mixture was washed with water and brine. It was dried overNa2SO4 and evaporated to give 2,2-dimethyl-3- (4- fluoro) phenylpropanal as an oil.

References:

WO2005/48932,2005,A2 Location in patent:Page/Page column 178