Water → N-(4-bromo-2-isopropylphenyl)acetamide

HRID 2108593Notes

Reaction equation

HRID 2108593 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH:9]([CH3:11])[CH3:10])[CH:3]=1.O.[C:13](OC(=O)C)(=[O:15])[CH3:14]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:13](=[O:15])[CH3:14])=[C:4]([CH:9]([CH3:11])[CH3:10])[CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 222719374-Bromo-2-(propan-2-yl)aniline

Product 1

HCID 20351194N-(4-bromo-2-isopropylphenyl)acetamideYield 83%

Procedure

A solution of 4-bromo-2-iso-propyl-phenylamine (780 mg, 3.64 mmol) in acetic anhydride (4 mL) was stirred at room temperature over night. The reaction was poured into water and the resulting white precipitate was filtered off and dried under vacuum to give N-(4-bromo-2-iso-propyl-phenyl)-acetamide as a light pink solid (0.770 g, 83%); 1H NMR (300 MHz, DMSO-d6): δ 9.39(s, 1H), 7.43(d, 1H, J=2.4 Hz), 3.16(m, 1H), 2.04(s, 3H), 1.13(d, 6H, J=7 Hz); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=dichloromethane; Rf=0.21

Workup

  1. filtrationthe resulting white precipitate was filtered off
  2. customdried under vacuum

Sources & evidence

ORD record
ord-e48b8f956a9a47fd9aaaf9f8dfc5f79a
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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