4-Chlorobenzonitrile → (1,1'-Biphenyl)-4-carbonitrile

HRID 1014777Notes

Reaction equation

HRID 1014777 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[F-].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2[C-](N(C)C)C=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:3][CH:4]=1)#[N:7]

Participants

7

Reactant 3

HCID 121634-ChlorobenzonitrileHCID 25953Cesium fluorideHCID 66827Phenylboronic Acid

Product 1

HCID 18021(1,1'-Biphenyl)-4-carbonitrileYield 92.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1317290462-Diphenylphosphino-dimethylaminoferroceneCatalystHCID 312751,4-DioxaneSolvent

Procedure

According to General Procedure A, a mixture 4-chlorobenzonitrile (69 mg, 0.50 mmol), phenylboronic acid (91 mg, 0.75 mmol), CsF (228 mg, 1.50 mmol), Pd(OAc)2 (2 mg, 0.01 mmol) and 12f (8 mg, 0.02 mmol) in 1,4-dioxane (2.5 mL) was heated to reflux, cooled and filtered. Evaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (5% Et2O in hexanes, silica gel) gave 51c (83 mg, 92%) as a colorless solid. 1H NMR (300 MHz, CDCl3) δ 7.69 (q, 4H, J=6 Hz), 7.61-7.57 (m, 2H), 7.52-7.40 (m, 3H); 13C NMR (75.5 MHz, CDCl3) δ 145.6, 139.1, 132.5, 129.0, 128.6, 127.6, 127.1, 118.8, 110.8.

Workup

  1. temperatureto reflux
  2. temperaturecooled
  3. filtrationfiltered
  4. customEvaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (5% Et2O in hexanes, silica gel)

Sources & evidence

ORD record
ord-fde6ac2bd60f4e98824e51ac1e645ca1
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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