1,10-Phenanthroline → 2,6-Dichlorobiphenyl

HRID 1848952Notes

Reaction equation

HRID 1848952 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=1.C(O[Li])(C)(C)C>[Cu]I.CN1C(=O)N(C)CCC1>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 109431,3-DichlorobenzeneHCID 11575IodobenzeneHCID 178506942HCID 178506942, compound

Product 1

HCID 363422,6-DichlorobiphenylYield 18%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

Copper(I) iodide (19 mg, 0.1 mmol), iodobenzene (204 mg, 1.0 mmol), 1,10-phenanthroline (18 mg, 0.1 mmol), 1,3-dichlorobenzene (220 mg, 1.5 mmol), tBuOLi (160 mg, 2.0 mmol), and DMPU (0.5 mL), 125° C., 12 hours. After column chromatography (hexanes) 40 mg (18%) of a colorless oil was obtained.

Sources & evidence

ORD record
ord-569b3fc85cac446496ab64546f0594df
Source dataset
uspto-grants-2015_02
Patent number
US08952207B2

Reaction notes

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