Acetyl chloride → N-(3-bromo-2-methylphenyl)acetamide

HRID 491224Notes

Reaction equation

HRID 491224 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:19](Cl)(=[O:21])[CH3:20]>>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:8][C:19](=[O:21])[CH3:20])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 1235383-Bromo-o-toluidine

Product 1

HCID 4162140N-(3-bromo-2-methylphenyl)acetamideYield 89%

Procedure

A solution of 3-bromo-2-methyl-phenylamine (4.1 g, 21.9 mmol) was treated with DIEA (8.4 mL, 48 mmol) and chilled to zero degrees. Acetyl chloride (1.7 mL, 24.1 mmol) was added dropwise via syringe. Reaction was allowed to return to room temperature and stir for 1 hour. Reaction was then poured onto water and washed once. Organic phase was evaporated to off-white solids. Trituration with hexanes afforded title compound as white solids (4.4 g, 89%).

Workup

  1. temperaturechilled to zero degrees
  2. customReaction
  3. customto return to room temperature
  4. customReaction
  5. additionwas then poured onto water
  6. washwashed once
  7. customOrganic phase was evaporated to off-white solids

Sources & evidence

ORD record
ord-7b3c460a5c304aca8015d12d337deebd
Source dataset
uspto-grants-2009_05
Patent number
US07528143B2

Reaction notes

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