Boron tribromide → 3-(4-Hydroxyphenyl)benzonitrile

HRID 1600912Notes

Reaction equation

HRID 1600912 reaction equation
B(Br)(Br)Br.[C:5]([C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)#[N:6]>ClCCl>[C:5]([C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)#[N:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 13936423-(4-Methoxyphenyl)benzonitrile

Product 1

HCID 37790963-(4-Hydroxyphenyl)benzonitrileYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of boron tribromide (1.0 M in dichloromethane, 38 ml) was added to a solution of 3'-cyano-4-methoxybiphenyl (4.0 g) in dichloromethane (150 ml) at -78 ° C. After the addition was complete the solution was allowed to warm to room temperature and was stirred for 18 hours. The solution was cooled to 0° C. and then ice (100 g) was added. The organic layer was separated and the aqueous phase extracted with ethyl acetate (3×100 ml). The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the sub-title compound as a cream solid (3.18 g).

Workup

  1. additionAfter the addition
  2. temperatureThe solution was cooled to 0° C.
  3. customThe organic layer was separated
  4. extractionthe aqueous phase extracted with ethyl acetate (3×100 ml)
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-71a21c5cb773481ea53efe8f54cf2dfe
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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