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

HRID 17276Notes

Reaction equation

HRID 17276 reaction equation
ClCCl.C([O:11][C:12]1[CH:13]=[C:14]([C:18]2[C:23]([CH3:24])=[C:22]([C:25]#[N:26])[C:21]([NH:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:20]([O:34]C)[C:19]=2[Br:36])[CH:15]=[CH:16][CH:17]=1)C1C=CC=CC=1.BrB(Br)Br.O>[Cl-].[Na+].O>[Br:36][C:19]1[C:20]([OH:34])=[C:21]([NH:27][C:28](=[O:33])[C:29]([CH3:31])([CH3:32])[CH3:30])[C:22]([C:25]#[N:26])=[C:23]([CH3:24])[C:18]=1[C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([OH:11])[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 86630800N-(3'-Benzyloxy-2-bromo-5-cyano-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

Product 1

HCID 86630804N-(2-Bromo-5-cyano-3,3'-dihydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamideYield 96%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  1. temperatureAfterwards, this was heated up to −12° C.
  2. stirringstirred for 1 hour
  3. temperatureheated up to 0° C.
  4. stirringstirred for 30 minutes
  5. customThe reaction liquid
  6. additionwas added
  7. extractionthe intended product was extracted with ethyl acetate (70 ml×2)
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-37177ec035d046dc9a43d6ccc514f427
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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