Dimethylformamide → Benzonitrile, 4-hydroxy-3-(1-methylethyl)- (9CI)

HRID 1271644Notes

Reaction equation

HRID 1271644 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:9]([CH3:11])[CH3:10])[CH:3]=1.[CH3:12][N:13](C=O)C>[C-]#N.[C-]#N.[Zn+2]>[C:12]([C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:9]([CH3:11])[CH3:10])[CH:3]=1)#[N:13]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 147934824-Bromo-2-(propan-2-yl)phenol

Product 1

HCID 18454722Benzonitrile, 4-hydroxy-3-(1-methylethyl)- (9CI)Yield 60%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

4-Bromo-2-isopropyl-phenol (500 mg, 2.3 mmol), Zn(CN)2 (270 mg, 2.3 mmol) and tetrakis(triphenylphosophine)palladium (237 mg) were mixed in DMF (1 mL) in a microwave reaction tube. It was reacted under microwave condition at 180° C. for 20 minutes. The mixture was filted and purified by by silica gel chromatography (40% -60% EtOAc/Hexane) to provide the title compound (220 mg, 60%). MS (DCI) m/z 162 (M+H)+.

Workup

  1. customIt was reacted under microwave condition at 180° C. for 20 minutes
  2. custompurified by by silica gel chromatography (40% -60% EtOAc/Hexane)

Sources & evidence

ORD record
ord-5ee23226059f4506b626808560cc6d54
Source dataset
uspto-grants-2007_04
Patent number
US07205409B2

Reaction notes

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