Benzene → 4-bromo-3-fluoro-4'-propyl-1,1'-Biphenyl

HRID 1755622Notes

Reaction equation

HRID 1755622 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](OB(O)O)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[Br:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][C:16]=1[F:22].C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C:7]2[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=2)=[CH:17][C:16]=1[F:22]

Participants

6

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 21869456HCID 21869456, compound

Product 1

HCID 199176444-bromo-3-fluoro-4'-propyl-1,1'-BiphenylYield 43.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 16.5 g of 4-propylphenylboric acid as dissolved in 130 ml of ethanol was dropwise added to a mixture comprising 30 g of 1-bromo-2-fluoro-4-iodobenzene, 1.6 g of tetrakistriphenylphosphine palladium(O), 186 ml of benzene and 140 ml of 2M aqueous sodium carbonate solution, in nitrogen atmosphere at room temperature. The reaction solution was then refluxed for 5 hours, cooled to room temperature, extracted with chloroform and washed three times with water, and chloroform was removed by distillation. The residue formed was distilled under reduced pressure (b.p. 155° to 170° C./3 mmHg) to obtain 11.7 g of 4-bromo-3-fluoro-4'-propylbiphenyl.

Workup

  1. temperatureThe reaction solution was then refluxed for 5 hours
  2. extractionextracted with chloroform
  3. washwashed three times with water, and chloroform
  4. customwas removed by distillation
  5. customThe residue formed
  6. distillationwas distilled under reduced pressure (b.p. 155° to 170° C./3 mmHg)

Sources & evidence

ORD record
ord-1adc520302504810a0ac6494c98ff875
Source dataset
uspto-grants-1995_08
Patent number
US05437815

Reaction notes

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