Water → Methyl acetyl(p-bromobenzoyl)acetate
Reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH:4]=[C:5](NC)[CH3:6].N1C=CC=CC=1.[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.[OH2:26]>C1COCC1>[CH3:1][O:2][C:3](=[O:9])[CH:4]([C:21](=[O:22])[C:20]1[CH:24]=[CH:25][C:17]([Br:16])=[CH:18][CH:19]=1)[C:5](=[O:26])[CH3:6]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To 3-methylamino-but-2-enoic acid methyl ester (5.0 g, 39.1 mmol) in THF (70 mL) was added pyridine (3.7 mL, 47 mmol) dropwise. The mixture was cooled to 0° C., and 4-bromobenzoyl chloride (8.55 g, 39.1 mmol) in THF (30 mL) was added dropwise. The reaction was stirred at room temperature overnight, and then water was added. The mixture was extracted with EtOAc, and the combined organic layers were washed with water, dried, filtered, and concentrated to give the title compound.
Workup
- extractionThe mixture was extracted with EtOAc
- washthe combined organic layers were washed with water
- customdried
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-039358ffc9374e99bf3f29932705080b
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440707B2
Reaction notes
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