ChemicalBook CAS DataBase List Oxazole, 2-(2,6-difluorophenyl)-4,5-dihydro-4,4-dimethyl-

Oxazole, 2-(2,6-difluorophenyl)-4,5-dihydro-4,4-dimethyl- synthesis

12synthesis methods

Product Name:Oxazole, 2-(2,6-difluorophenyl)-4,5-dihydro-4,4-dimethyl-
CAS Number:66464-26-4
Molecular formula:C11H11F2NO
Molecular Weight:211.21

Benzamide, 2,6-difluoro-N-(2-hydroxy-1,1-dimethylethyl)-

150079-31-5
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Oxazole, 2-(2,6-difluorophenyl)-4,5-dihydro-4,4-dimethyl-

66464-26-4
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Yield:66464-26-4 90%

Reaction Conditions:

Stage #1: N-(2-hydroxy-1,1-dimethylethyl)-2,6-difluorobenzamidewith thionyl chloride in dichloromethane at 0; for 1 h;
Stage #2: with sodium hydroxide in water;

Steps:

15

To an ice-bath cooled solution OF 2, 6-DIFLUORO-N- (2-HYDROXY-1, 1- dimethylethyl) benzamide (Description 14, 60.28 g, 263 mmol) in anhydrous dichloromethane (250 ml), THIONYL chloride (30.62 ml, 421 mmol) was added dropwise. After complete addition the ice bath was removed and the mixture stirred for 1 hour. The solvent was evaporated and the residue triturated with diethyl ether. The resultant solid was dissolved in water (200 ml) and basified by the addition of solid NAOH. The mixture was extracted with ethyl acetate (3 x 200 ml), the combined organic layers washed with brine, dried over NA2SO4, filtered and evaporated. The residue was purified by column chromatography on silica (eluting with 20% EtOAc in isohexanes) to give the title compound (50 g, 90%). 1H NMR (500 MHz, CDC13) 8 1.42 (6H, s), 4.13 (2H, s), 6.94 (2H, t, J8. 3 and 8.1), 7.37 (1H, M).

References:

WO2005/28445,2005,A2 Location in patent:Page/Page column 31