Boron tribromide → 3-Hydroxy-5-(trifluoromethyl)benzonitrile

HRID 873081Notes

Reaction equation

HRID 873081 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)[C:6]#[N:7]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 269863073-Methoxy-5-(trifluoromethyl)benzonitrile

Product 1

HCID 534131963-Hydroxy-5-(trifluoromethyl)benzonitrileYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxy-5-(trifluoromethyl)benzonitrile (1.30 g, 6.46 mmol) in dry dichloromethane (30 mL) was added BBr3 (0.0920 mL, 0.969 mmol) at 0° C. The reaction mixture was stirred at rt for two days, quenched with 10% sodium bicarbonate (50 mL) and extracted with DCM (2×200 mL). Combined organic portions were dried over anhydrous sodium sulphate and concentrated to afford the title product (1.1 g).

Workup

  1. customquenched with 10% sodium bicarbonate (50 mL)
  2. extractionextracted with DCM (2×200 mL)
  3. dry with materialCombined organic portions were dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-80907c91cea8495eb61eee847f100761
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

Loading…