Acetyl chloride → 3-METHYL-4-BROMOACETANILIDE

HRID 1741055Notes

Reaction equation

HRID 1741055 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:17](=[O:19])[CH3:18])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 233594-Bromo-3-methylaniline

Product 1

HCID 7383363-METHYL-4-BROMOACETANILIDEYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-bromo-3-methylaniline (3.0 g, 0.016 mole) and triethylamine (4.5 ml, 0.032 mole) in dichloromethane (30 ml) at 0° C. was treated with acetyl chloride (1.2 ml, 0.017 mole) and allowed to warm to room temperature over 1 h. The mixture was washed with water, then 5M HCl acid and dried (Na2SO4), then concentrated in vacuo to afford the title compound as a pale yellow solid (3.07 g, 83%).

Workup

  1. washThe mixture was washed with water
  2. dry with material5M HCl acid and dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d28f1801c2341b9be6749130abf8973
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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