Acetyl chloride → N-(2-Bromo-5-nitrophenyl)acetamide
Reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].CCN(C(C)C)C(C)C.[C:21](Cl)(=[O:23])[CH3:22]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH:4][C:21](=[O:23])[CH3:22]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
2-Bromo-5-nitroaniline (10 g) was dissolved in CH2Cl2 (500 mL), DIEA (6.6 g) was added to the mixture, followed by 100 mg of DMAP. The mixture was cooled to 0° C. in ice bath. Acetyl chloride (4 g in 50 mL CH2Cl2) was added dropwise to the reaction mixture. After the mixture was stirred at RT over 3 h, and extracted once with saturated NaHCO3 solution and once with brine. The resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 1:1 EtOAc:Hexane to 100% EtOAc to afford a white solid. MS: 258 (M−1). Calc'd. for C8H7BrN2O3—259.1.
Workup
- extractionextracted once with saturated NaHCO3 solution and once with brine
- dry with materialThe resulting organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude material was purified by flash chromatography on silica gel with 1:1 EtOAc
- customHexane to 100% EtOAc to afford a white solid
Sources & evidence
- ORD record
- ord-09895d0522de4dcba593bbaf38c2ddea
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687643B2
Reaction notes
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