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

HRID 1047032Notes

Reaction equation

HRID 1047032 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])=[CH:4][CH:3]=1.C[Si](C)(C)[O-:15].[K+].O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:12])([CH3:11])[C:9]([NH2:10])=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 177506012-(4-Bromophenyl)-2-methylpropanamideYield 92.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(4-bromophenyl)-2-methylpropanenitrile (3.29 g) in toluene (33 mL) was added potassium trimethylsilanolate (8.37 g) portionwise. After being stirred at reflux temperature for 5 h, the reaction mixture was cooled to room temperature. Water(17 mL) was added to the mixture dropwise. Filtration gave the product (3.28 g, 92%). 1HNMR (CDCl3) 400 MHz δ: 7.49 (d, J=8.7 Hz, 2H), 7.28 (d, J=8.7 Hz, 2H), 5.52-4.93 (m, 2H), 1.57 (s, 6H).

Workup

  1. temperatureat reflux temperature for 5 h
  2. filtrationFiltration

Sources & evidence

ORD record
ord-e7b220edb3d547989cc0c4dc36066a23
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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