Potassium Carbonate → 2'-Fluoro-6-hydroxy-5-nitrobiphenyl-3-carbonitrile

HRID 2093629Notes

Reaction equation

[OH:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1I.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:3]1[C:2]([OH:1])=[C:9]([N+:10]([O-:12])=[O:11])[CH:8]=[C:5]([C:6]#[N:7])[CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 4-hydroxy-3-iodo-5-nitrobenzonitrile (870 mg) and 2-fluorophenylboronic acid (630 mg) in acetone (50 ml) and water (12.5 ml) was added the palladium(II) acetate (73 mg) and potassium carbonate (830 mg). The reaction was then heated for 18 h at 60° C. The mixture was then concentrated in vacuo and filtered through a plug of silica gel, eluting with ethyl acetate. The eluent was concentrated in vacuo and the residue was purified via flash chromatography on a Biotage Horizon, 40 M column, eluting with 1 column volume of 100% hexanes, followed by a gradient of 0-40% ethyl acetate in hexanes over 10 column volumes to provide the title compound (668 mg, 86%). Mass spectrum (ESI) 257.1 (M−1).

Workup

concentrationThe mixture was then concentrated in vacuo
filtrationfiltered through a plug of silica gel
washeluting with ethyl acetate
concentrationThe eluent was concentrated in vacuo
customthe residue was purified via flash chromatography on a Biotage Horizon, 40 M column
washeluting with 1 column volume of 100% hexanes

Sources & evidence

ORD record: ord-08714d7230394c178b08465de04ef6aa
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445480B2

Reaction notes

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