Bromide ion → HCID 21942497, compound

HRID 1791346Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:5]=[C:6](Br)[CH:7]=1.[Br-].[CH3:15][N:16](C=O)C>[C-]#N.[Zn+2].[C-]#N.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:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:5]=[C:6]([C:15]#[N:16])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 3-fluoro-5-bromo-(1H-imidazol-1-yl)-benzene in DMF (36 mL) was treated with zinc cyanide and tetrakis(triphenylphosphine)palladium(0). The reaction mixture was heated under an argon atmosphere for 18 h at 80° C. when GC-MS indicated complete disappearance of starting bromide and presence of product molecular ion (M+ 187). The reaction mixture was partitioned between ethyl acetate and water, filtered to remove insoluble material, and the layers obtained in the filtrate were separated. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. 3-Fluoro-5-cyano-(1H-imidazol-1-yl)-benzene was obtained as a colourless solid and used without further purification.

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
filtrationfiltered
customto remove insoluble material
customthe layers obtained in the filtrate
customwere separated
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5b79f67932a94e14accfc8c088e94cde
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074809B2

Reaction notes

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