2-Bromo-1-fluoro-4-nitrobenzene → 1-(2-Fluoro-5-nitrophenyl)ethan-1-one

HRID 1593066Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].C([Sn](CCCC)(CCCC)[C:17]([O:19]CC)=[CH2:18])CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:8][C:7]1[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=1[C:17](=[O:19])[CH3:18]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3-bromo-4-fluoronitrobenzene (696 mg, 3.16 mmol) and tributyl(1-ethoxyvinyl)tin (1.07 ml, 3.5 mmol) in 10 mL toluene, was added tetrakis(triphenylphosphine)palladium(0) (183 mg, 016 mmol). The mixture was purged with argon for 3 minutes, and then heated to 110° C. under argon for 2 days. The reaction mixture was cooled to room temperature, 3 mL 1 N HCl was added and stirred at room temperature for 40 minutes. Workup followed by column chromatographic purification (silica 10%-30% EtOAc/hexane) to give pure 1-(2-fluoro-5-nitro-phenyl)-ethanone.

Workup

customThe mixture was purged with argon for 3 minutes
temperatureThe reaction mixture was cooled to room temperature
addition3 mL 1 N HCl was added
customWorkup followed by column chromatographic purification (silica 10%-30% EtOAc/hexane)

Sources & evidence

ORD record: ord-5cc20239cc5c4f52897c0973ba2d4ce6
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07294635B2

Reaction notes

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