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

HRID 1170954Notes

Reaction equation

HRID 1170954 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-8d4a42d9ab514bc1a39e308b656ad827
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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