4-Chloroaniline → 2-Bromo-N-(4-chlorophenyl)propanamide

HRID 868836Notes

Reaction equation

HRID 868836 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Br:9][CH:10]([CH3:14])[C:11](Cl)=[O:12]>ClCCl.O>[Br:9][CH:10]([CH3:14])[C:11]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:12]

Participants

5

Reactant 2

HCID 78124-ChloroanilineHCID 979802-Bromopropanoyl chloride

Product 1

HCID 126745972-Bromo-N-(4-chlorophenyl)propanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloroaniline (400 mg, 3.13 mmol) in anhydrous dichloromethane at room temperature under N2 was added slowly 2-bromopropanoyl chloride (474 μL, 4.7 mmol). The reaction mixture was stirred at room temperature for 2 h and then diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The organic extracts were combined, washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo to give 2-bromo-N-(4-chlorophenyl)propanamide, which was used without further purifications.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d123a7653263404eb3407a89978a65c8
Source dataset
uspto-grants-2015_03
Patent number
US08969342B2

Reaction notes

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