Acetyl chloride → N-(3-Bromophenyl)acetamide

HRID 1836348Notes

Reaction equation

HRID 1836348 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Br:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9].C(N(CC)CC)C>O1CCCC1>[CH3:2][C:1]([NH:9][C:8]1[CH:10]=[CH:11][CH:12]=[C:6]([Br:5])[CH:7]=1)=[O:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 115623-Bromoaniline

Product 1

HCID 12123N-(3-Bromophenyl)acetamideYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of acetyl chloride (44.0 ml, 0.619 mol) in tetrahydrofuran (20 ml) was added dropwise to a 0° C. solution of 3-bromoaniline (101.5 g, 0.590 mol) and triethylamine (87.4 ml, 0.625 mol) in tetrahydrofuran (550 ml). The resulting mixture was stirred 16 h at room temperature. The reaction mixture was quenched with ice/water (500 ml), acidified to pH 1 with 5N hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate extracts were washed with 1N hydrochloric acid, water, brine, then dried over sodium sulfate. The solvent was removed under reduced pressure to give 125.5 g of a red solid. Recrystallization from ethyl acetate/hexanes gave 69.2 g of an off white powder. Filtered a second crop of product to give 26 g of a tan powder. Total yield=75%.

Workup

  1. customThe reaction mixture was quenched with ice/water (500 ml)
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate extracts were washed with 1N hydrochloric acid, water, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-99c7d322649240e2b2a304e23c70bacb
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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