4-Chloroaniline → 2-Bromo-N-(4-chlorophenyl)propanamide
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
Product 1
Reagents, catalysts & solvents 2
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
- extractionextracted with ethyl acetate (3×50 mL)
- washwashed with brine
- dry with materialdried over anhydrous MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-d123a7653263404eb3407a89978a65c8
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969342B2
Reaction notes
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