Water → 4'-Bromoacetanilide

HRID 2093043Notes

Reaction equation

HRID 2093043 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:16](OC(=O)C)(=[O:18])[CH3:17].O>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:16](=[O:18])[CH3:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78074-BromoanilineHCID 7918Acetic AnhydrideHCID 8471Triethylamine

Product 1

HCID 76834'-BromoacetanilideYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-bromoaniline (1.0 eq) in dichloromethane, triethylamine (2.2 eq) was added at 0° C. and stirred for 15 min. To this mixture was added acetic anhydride (1.0 eq) in dichloromethane at 0° C., after addition the reaction was continued at room temperature for 5 hrs. Water was added and the organic layer was separated, dried over anhydrous Na2SO4, concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the desired N-(4-bromophenyl)acetamide. (Yield=65%)

Workup

  1. additionafter addition the reaction
  2. waitwas continued at room temperature for 5 hrs
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude product, which
  7. customon purification by column chromatography

Sources & evidence

ORD record
ord-fea545f40b4645dd96b2fea6820355b8
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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