Water → 2-(4-Bromophenyl)-2-methylpropanamide

HRID 229773Notes

Reaction equation

HRID 229773 reaction equation
C[Si](C)(C)[O-].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:17]#[N:18])([CH3:16])[CH3:15])=[CH:10][CH:9]=1.[OH2:19]>C1(C)C=CC=CC=1>[NH2:18][C:17]([C:14]([C:11]1[CH:10]=[CH:9][C:8]([Br:7])=[CH:13][CH:12]=1)([CH3:16])[CH3:15])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 104435912-(4-Bromophenyl)-2-methylpropanenitrile2×HCID 23668039Potassium trimethylsilanolate

Product 1

HCID 177506012-(4-Bromophenyl)-2-methylpropanamideYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Potassium trimethylsilanolate (purity: 90%)(250 g, 1,800 mmol) was added at room temperature to a solution of 100 g (450 mmol) of 1-bromo-4-(1-cyano-1-methylethyl)benzene (referential compound 1-1) in 1,000 ml of toluene with stirring in an argon stream and the mixture was stirred for 4.5 hours under a condition of heating to reflux. After the reaction was finished, the reaction solution was cooled down to room temperature and 500 ml of water was dropped thereinto. The mixed solution was stirred for 25 minutes at room temperature and the resulting solid was filtered off and washed with 400 ml of water to give 99 g of the title compound as white powder (yield: 92%).

Workup

  1. stirringthe mixture was stirred for 4.5 hours under a condition
  2. temperatureof heating to reflux
  3. stirringThe mixed solution was stirred for 25 minutes at room temperature
  4. filtrationthe resulting solid was filtered off
  5. washwashed with 400 ml of water

Sources & evidence

ORD record
ord-5ae308660f1a4cc4be8141b651e3bd1e
Source dataset
uspto-grants-2009_07
Patent number
US07563906B2

Reaction notes

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