Acetyl chloride → N-(3-Bromophenyl)acetamide

HRID 491223Notes

Reaction equation

HRID 491223 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:18](Cl)(=[O:20])[CH3:19]>>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:18](=[O:20])[CH3:19])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 115623-BromoanilineHCID 81531Diisopropylethylamine

Product 1

HCID 12123N-(3-Bromophenyl)acetamide

Procedure

A solution of 3-bromo-phenylamine (1.04 g, 6 mmol) was treated with DIEA (2.3 mL, 13.3 mmol) and chilled to zero degrees. Acetyl chloride (0.47 mL, 6.7 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 beige solids (1.25 g, 98%).

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 beige solids (1.25 g, 98%)

Sources & evidence

ORD record
ord-78a09c48fd2248b080ba7006337f4575
Source dataset
uspto-grants-2009_05
Patent number
US07528143B2

Reaction notes

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