Реакция #45554

Уравнение реакции

water

dichloromethane

N-(3′-benzyloxy-2-bromo-5-cyano-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

dichloromethane

tribromoborane

→

compound

Выход 96.0%

N-(2-Bromo-5-cyano-3,3′-dihydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

Выход 96.0%

Растворители

brine

Условия реакции

Обработка

1. 1
   ТемператураAfterwards, this was heated up to −12° C.
2. 2
   workup.STIRRINGstirred for 1 hour
3. 3
   Температураheated up to 0° C.
4. 4
   workup.STIRRINGstirred for 30 minutes
5. 5
   ДругоеThe reaction liquid
6. 6
   workup.ADDITIONwas added
7. 7
   Экстракцияthe intended product was extracted with ethyl acetate (70 ml×2)
8. 8
   СушкаThe organic layer was dried over anhydrous magnesium sulfate
9. 9
   Концентрированиеconcentrated under reduced pressure
10. 10
    Другоеthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Методика

A dichloromethane (18 ml) solution of N-(3′-benzyloxy-2-bromo-5-cyano-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide (I-13) (620 mg, 1.22 mmol) was cooled at −78° C., a dichloromethane solution of 1 N tribromoborane (3.67 ml, 3.67 mmol) was dropwise added, followed by stirring at −78° C. for 20 minutes. Afterwards, this was heated up to −12° C. and stirred for 1 hour, then heated up to 0° C. and stirred for 30 minutes. The reaction liquid was put into cold water (50 ml), saturated brine (50 ml) was added, the intended product was extracted with ethyl acetate (70 ml×2). The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the entitled compound (457 mg, 96%) as a yellow white semi-solid.

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