1-Bromo-3-fluorobenzene → 1,1'-Biphenyl, 3-fluoro- (9CI)

HRID 241318Notes

Reaction equation

HRID 241318 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)(C)C>[F:8][C:4]1[CH:3]=[C:2]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 140821-Bromo-3-fluorobenzeneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic Acid

Product 1

HCID 1456631,1'-Biphenyl, 3-fluoro- (9CI)

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

12.27 g (70.2 mmol, 1 eq.) of 1-bromo-3-fluorobenzene and 44.7 g (210.5 mmol, 3 eq.) of K3PO4 are added to a solution of 12.83 g (105.3 mmol, 1.5 eq.) of phenylboronic acid in 200 ml of isopropanol. The mixture is stirred at room temperature for 4 hours. 0.0021 g (14.8 μmol, 0.0021 mol %) of [{Pd[P(C2F5)2O]2H}2(μ-Cl)2], prepared in accordance with Example 13, is subsequently added, and the reaction mixture is stirred at room temperature for 20 hours, giving 3-fluorobiphenyl quantitatively.

Workup

  1. additionis subsequently added
  2. stirringthe reaction mixture is stirred at room temperature for 20 hours

Sources & evidence

ORD record
ord-7d892e195e7440658139aa253ad9083c
Source dataset
uspto-grants-2014_02
Patent number
US08648202B2

Reaction notes

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