Boron tribromide → 2-(3-Hydroxyphenyl)acetonitrile

HRID 567855Notes

Reaction equation

HRID 567855 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1.C([O-])(O)=O.[Na+]>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 88310(3-Methoxyphenyl)acetonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 137810422-(3-Hydroxyphenyl)acetonitrileYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (68 ml, 1M in dichloromethane, 68 mmol) was added dropwise to an ice-cooled solution of (3-methoxyphenyl)acetonitrile (5.0 g, 34 mmol) in dichloromethane (50 ml), and once addition was complete, the reaction was allowed to warm to room temperature and stirred overnight. The reaction was poured into an ice/water solution, the mixture was basified using NaHCO3 and extracted with dichloromethane. The combined organic extracts were dried over MgSO4 and evaporated under reduced pressure to give the desired product as a brown oil, (4.13 g, 91%).

Workup

  1. temperaturecooled
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6e4971d4548b4aaa8026956e10bb0163
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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