4-Chlorobenzonitrile → 4-Cyano-4'-(Trifluoromethyl)biphenyl

HRID 412799Notes

Reaction equation

HRID 412799 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.[F-].[K+]>C1COCC1>[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 121634-ChlorobenzonitrileHCID 522689Potassium FluorideHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 43684634-Cyano-4'-(Trifluoromethyl)biphenylYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chlorobenzonitrile (141 mg, 1.02 mmol) reacted with p-trifluoromethylphenylboronic acid using by 1/2 mol % of Pd(OAc)2/Ph5FcP(t-Bu)2 and KF (182 mg, 3.00 mmol) in THF solvent to give the title compound (236 mg, 96%) as a white solid after recrystallization from hexane: 1H-NMR (500 MHz, CDCl3): δ 7.78 (d, 2H, J=8.23 Hz), 7.76 (d, 2H, J=8.48 Hz), 7.71 (app.d, 4H, J=8.18 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 111.92, 118.57, 142.61, 144.09, 123.95 (q, J=270.2 Hz), 126.04 (q, J=3.6 Hz), 127.60, 127.93, 130.63 (q, J=32.5 Hz), 132.76. 19F{1H}-NMR (MHz, CDCl3): δ −63.0. GC/MS(EI): m/z 247 (M+).

Sources & evidence

ORD record
ord-97d14b51edfd4e798fc218b573ea78df
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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