Chlorobenzene → Biphenyl

HRID 412829Notes

Reaction equation

HRID 412829 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(B(O)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[F-].[K+]>C1COCC1>[C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7964ChlorobenzeneHCID 66827Phenylboronic AcidHCID 522689Potassium Fluoride

Product 1

HCID 7095BiphenylYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chlorobenzene (56 mg, 0.50 mmol) reacted with phenylboronic acid (92 mg, 0.75 mmol) using 0.5/1.0 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (87 mg, 1.50 mmol) in THF solvent at 45° C. to give the title compound (74 mg, 96%) as a white solid.

Workup

  1. customat 45° C.

Sources & evidence

ORD record
ord-11a28f8228874516a4baf4c086c9cdc5
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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