Water → Methyl acetyl(p-bromobenzoyl)acetate

HRID 553661

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

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-6b5161bf103c4a3fb0b47f7e1ce1a3b0
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048902B2

Linked notes

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