Acetic Anhydride → Ethyl 2-(3-bromo-2,4,5-trifluorobenzoyl)-3-ethoxyacrylate

HRID 1761651Notes

Reaction equation

[Br:1][C:2]1[C:3]([F:18])=[C:4]([CH:13]=[C:14]([F:17])[C:15]=1[F:16])[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6].[CH:19]([O-])([O-])[O:20][CH2:21][CH3:22].C(OC(=O)C)(=O)C>>[Br:1][C:2]1[C:3]([F:18])=[C:4]([CH:13]=[C:14]([F:17])[C:15]=1[F:16])[C:5]([C:7](=[CH:19][O:20][CH2:21][CH3:22])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 10592111Ethyl 3-bromo-2,4,5-trifluorobenzoylacetate

HCID 53630039Ethylorthoformate

Product 1

HCID 54232143Ethyl 2-(3-bromo-2,4,5-trifluorobenzoyl)-3-ethoxyacrylateYield 99.5%

Conditions

Temperature: 130 °C

Procedure

A mixture of ethyl 3-bromo-2,4,5-trifluorobenzoylacetate (1.5 g), ethyl orthoformate (1.0 g) and acetic anhydride (1.2 g) was stirred at 130° C. for 4.5 hours and then concentrated to give the title compound (1.75 g) as yellow oil.

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-3df0a3e839aa47b588a6a3e3ad71faaa
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04826982

Reaction notes

Loading…