1,3-Dibromobenzene → 3-Bromo-4'-chloro-biphenyl

HRID 726603Notes

Reaction equation

HRID 726603 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](Br)[CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:14]2[CH:13]=[C:12]([Br:11])[CH:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 79271,3-DibromobenzeneHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acid

Product 1

HCID 27568743-Bromo-4'-chloro-biphenyl

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

This compound is prepared in a manner analogous to that of Step D of Example 4, using 6.9 grams (0.044 mole) of 4-chlorophenylboronic acid (commercially available), 25.0 grams (0.100 mole) of 1,3-dibromobenzene, 0.2 gram (catalyst) of tetrakis(triphenylphosphine)palladium(O), 75 mL of aqueous 2M sodium carbonate, and 75 mL of toluene, yielding 3-(4-chlorophenyl)phenyl bromide.

Workup

  1. customThis compound is prepared in a manner analogous to that of Step D of Example 4

Sources & evidence

ORD record
ord-35928e09b0514cfaa491597f46e1284f
Source dataset
uspto-grants-1998_01
Patent number
US05710157

Reaction notes

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