Fluorobenzene → 4-Bromo-2-fluoro-1,1'-biphenyl

HRID 1656854Notes

Reaction equation

HRID 1656854 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:10][C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:12]=1I.FC1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.[Pd]>[F:10][C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:12]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 10008FluorobenzeneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 27245164-Bromo-2-fluoro-1-iodobenzene

Product 1

HCID 5210634-Bromo-2-fluoro-1,1'-biphenylYield 10%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Using methodology generally similar to the above examples, 1.22 g of phenylboronic acid in about 5 ml of ethanol, 3 g of 2-fluoro-4-bromoiodobenzene, 20 g of fluorobenzene, 0.2 g of 5% Pd on carbon catalyst, and 10 ml of 2 molar Na2CO3 were combined and stirred rapidly (without a nitrogen purge) at 25° C. for 65 hours. The desired 2-fluoro-4-bromobiphenyl was produced in about 10% yield with only partial conversion of the starting materials, considerable byproduct formation, but no observed terphenyl formation.

Workup

  1. custompurge) at 25° C. for 65 hours

Sources & evidence

ORD record
ord-7d0e5e7273064dd2a4ce390c8198263c
Source dataset
uspto-grants-1993_10
Patent number
US05254776

Reaction notes

Loading…