تفاعل #45554

معادلة التفاعل

water

dichloromethane

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

dichloromethane

tribromoborane

→

compound

المردود 96.0%

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

المردود 96.0%

المذيبات

brine

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر