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1192040-50-8

1H-Isoindol-1-one, 5,6-difluoro-2,3-dihydro- synthesis

3synthesis methods
1H-Isoindol-1-one, 5,6-difluoro-2,3-dihydro-3-hydroxy-

1192040-49-5
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1H-Isoindol-1-one, 5,6-difluoro-2,3-dihydro-

1192040-50-8
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Yield:1192040-50-8 10.6%

Reaction Conditions:

with triethylsilane;trifluoroacetic acid in dichloromethane at 20;

Steps:

293A

748 mg of 5,6-difluoro-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (crude product, about 4.04 mmol) were initially charged in 50 ml of dichloromethane, 3.8 ml (48.5 mmol) of trifluoroacetic acid and 1.3 ml (8.08 mmol) of triethylsilane were added and the mixture was stirred overnight at RT. The reaction mixture was then concentrated, and the residue was dissolved in dichloromethane and washed with sodium bicarbonate solution. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 1:1 to 0:1). This gave 72 mg (10.6% of theory) of the target compound.LC-MS (method 15): Rt=0.61 min; m/z=170 (M+H)+.1H-NMR (400 MHz, DMSO-d6): δ=8.74 (br. s, 1H), 7.76-7.64 (m, 2H), 4.36 (s, 2H).

References:

US2011/34450,2011,A1 Location in patent:Page/Page column 114