Water → HCID 59458590, compound

HRID 1874200Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:9]([C:11]2[CH:16]=[C:15]([O:17][C:18]([F:23])([F:22])[CH:19]([F:21])[F:20])[CH:14]=[C:13]([F:24])[CH:12]=2)=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].O.[CH3:26][N:27](C=O)C>[C-]#N.[Zn+2].[C-]#N>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9](=[O:10])[C:11]2[CH:16]=[C:15]([O:17][C:18]([F:23])([F:22])[CH:19]([F:21])[F:20])[CH:14]=[C:13]([F:24])[CH:12]=2)=[CH:3][C:2]=1[C:26]#[N:27]

Participants

Conditions

Temperature: 175 °C

Procedure

A mixture of (3-bromo-4-fluorophenyl)(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)methanone, prepared as described in Procedure 3 and 62, (2.0 g, 4.84 mmol), zinc cyanide (568 mg, 4.84 mmol) and tetrakis(triphenyphoshine)palladium (559 mg, 0.48 mmol) in DMF was heated at 175° C. under microwave irradiation for 10 minutes. The reaction mixture was allowed to cool to room temperature, poured into H2O and the aqueous layer was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by ISCO chromatography (12 g column, 0-20% EtOAc/hexane) to yield 2-fluoro-5-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)benzoyl)benzonitrile as a colorless oil (1.5 g, 86% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.11 (m, 2H), 7.41 (m, 3H), 7.27 (m, 1H), 5.97 (m, 1H).

Workup

customprepared
temperatureto cool to room temperature
extractionthe aqueous layer was extracted with EtOAc
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by ISCO chromatography (12 g column, 0-20% EtOAc/hexane)

Sources & evidence

ORD record: ord-85aa75f72ba4413d9af6d1df69275c8e
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304403B2

Reaction notes

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