Acetic Anhydride → N-(2-Bromo-4-isopropylphenyl)acetamide

HRID 1725866Notes

Reaction equation

HRID 1725866 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:12](OC(=O)C)(=[O:14])[CH3:13].C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:12](=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 5213372-Bromo-4-isopropylaniline

Product 1

HCID 258023N-(2-Bromo-4-isopropylphenyl)acetamideYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-bromo-4-isopropylaniline (5.05 g, 23.6 mmol), acetic anhydride (2.4 mL, 25 mmol), and triethylamine (3.5 mL, 25 mmol) in dichloromethane (25 mL) was stirred at ambient temperature for 4 days. The mixture was diluted with dichloromethane, washed sequentially with saturated aqueous Na2CO3 and 1M HCl, dried (MgSO4), filtered, and concentrated to provide the desired product (5.85 g). MS (DCI) m/e 256, 258 (M+H)+; 273, 275 (M+NH4)+.

Workup

  1. washwashed sequentially with saturated aqueous Na2CO3 and 1M HCl
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4231c22b169e4caf978815a54b69cbe5
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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