Water → N-(4-bromo-2-ethylphenyl)acetamide

HRID 341683

Reaction equation

HRID 341683 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH2:9][CH3:10])[CH:3]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19].O>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18](=[O:20])[CH3:19])=[C:4]([CH2:9][CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 28012834-Bromo-2-ethylaniline

Product 1

HCID 2735223N-(4-bromo-2-ethylphenyl)acetamideYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-ethylaniline (50 g, 0.25 mol) in dichloromethane (250 ml) is added triethylamine (63.24 g, 0.62 mol) and the mixture is stirred at room temperature for 30 minutes. The reaction mixture is cooled to 0° C. and acetyl chloride (39.25 g, 0.5 mol) is added dropwise. The reaction mixture is stirred at 25-30° C. for 60 minutes, then poured into water, and the two phases separated. The organic phase is washed with water, dried over anhydrous sodium sulfate, filtered and the filtrate is evaporated under reduced pressure to yield N-(4-bromo-2-ethylphenyl)acetamide (40 g).

Workup

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. stirringThe reaction mixture is stirred at 25-30° C. for 60 minutes
  3. customthe two phases separated
  4. washThe organic phase is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-ab06096ecef34f869695e9d0f193cf6a
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Linked notes

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