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

HRID 1839918Notes

Reaction equation

HRID 1839918 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Br:8].[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1>C1(C)C=CC=CC=1.C(O)C.C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:13]1[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=1

Participants

7

Reactant 2

HCID 114141,2-DibromobenzeneHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 132706302-Bromo-4'-fluoro-1,1'-biphenylYield 82.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Procedure

Under nitrogen, 1.2 g (1.0 mmol) of Pd(PPh3)4 was added to a stirred solution of 9.9 g (42 mmol) of 1,2-dibromobenzene (Aldrich) and 3.0 g (21 mmol) of 4-fluorophenylboronic acid in 42 mL of toluene, 42 mL of ethanol and 42 mL of 2M Na2CO3. After vigorous stirring at reflux for 3 hours, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate. The resulting solution was washed with water and dried over MgSO4. Purification by silica gel chromatography (Waters Prep-500A) with hexane gave 4.35 g (81%) of 1-bromo-2-(4-fluorophenyl)benzene as a colorless oil: NMR (CDCl3) δ 7.07-7.26 (m, 3H), 7.27-7.44 (m, 4H), 7.67 (d, J=8 Hz, 1H).

Workup

  1. temperatureat reflux for 3 hours
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe resulting solution was washed with water
  5. dry with materialdried over MgSO4
  6. customPurification by silica gel chromatography (Waters Prep-500A) with hexane

Sources & evidence

ORD record
ord-f90ff3a3aa9941cd993160d116cf5fc0
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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