1-Bromo-2-fluorobenzene → 2-Fluoro-3'-methyl-1,1'-biphenyl

HRID 1731802Notes

Reaction equation

HRID 1731802 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[Mg]Br.Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17]>CCOCC>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:3]1[CH:2]=[C:1]([CH3:9])[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 612591-Bromo-2-fluorobenzeneHCID 178424303HCID 178424303, compound

Product 1

HCID 128530412-Fluoro-3'-methyl-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 1.46M solution (45 ml) of toluylmagnesium bromide in ether was added to a mixture of 10 g 2-bromofluorobenzene and 250 mg bis(diphenylphosphinoethane)-nickel dichloride in 70 ml dry diethyl ether. The mixture was then heated at reflux for 18 hours. The mixture was cooled to room temperature and quenched with 10% aqueous ammonium chloride, followed by 1M hydrochloric acid, and then partitioned between ether and water. The aqueous phase was extracted once more with ether and the combined organic extracts were dried and evaporated yielding the crude product as an oil which was purified by elution from silica gel with hexanes. The product was a colorless oil (7.0 g, 66% yield) which was used without further purification. NMR (CDCl3, 60MHz): 7.4-6.9 (m, 8H), 2.4 (s, 3H).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 18 hours
  3. customquenched with 10% aqueous ammonium chloride
  4. custompartitioned between ether and water
  5. extractionThe aqueous phase was extracted once more with ether
  6. customthe combined organic extracts were dried
  7. customevaporated

Sources & evidence

ORD record
ord-440c92d0d1624000881e0716d35d0f8d
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

Loading…