2-Bromonaphthalene → 2-(3-Fluorophenyl)naphthalene

HRID 1712190Notes

Reaction equation

HRID 1712190 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[F:12][C:13]1[CH:14]=[C:15](OB(O)O)[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.O.C(O)C>[F:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=2)[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 113722-BromonaphthaleneHCID 11430Potassium CarbonateHCID 222378213-Fluorophenylboric acid

Product 1

HCID 542381022-(3-Fluorophenyl)naphthaleneYield 84.6%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

A mixture of 10.00 g (=47.33 mmol) of 2-bromonaphthalene, 7.95 g (=56.82 mmol) of 3-fluorophenylboric acid, 9.81 g (=70.98 mmol) of K2CO3, 3.81 g (=11.82 mmol) of tetrabutylammonium bromide, 1.00 g (=1.42 mmol) of dichlorobis(triphenylphosphine) palladium(II), 0.76 g (=2.84 mmol) of triphenylphosphine and a 100 ml mixed solvent of toluene/water/ethanol in a ratio of 1:1:1 was stirred for 7 hours with reflux. The reaction mixture obtained was extracted twice with toluene. The extract was washed thrice with water and then dried with anhydrous MgSO4. After the solvent was evaporated under a reduced pressure, the obtained black solid of 15.40 g was purified with silica gel chromatography using heptane/toluene in a ratio of 5:1 as the eluent, thereby obtaining a white solid of 10.98 g. The white solid was recrystallized with a mixed solvent of Solumix/heptane in a ratio of 1:1 to obtain 8.90 g of 2-(3-fluorophenyl)naphthalene as white crystals.

Workup

  1. temperaturewith reflux
  2. customThe reaction mixture obtained
  3. extractionwas extracted twice with toluene
  4. washThe extract was washed thrice with water
  5. dry with materialdried with anhydrous MgSO4
  6. customAfter the solvent was evaporated under a reduced pressure
  7. customthe obtained black solid of 15.40 g was purified with silica gel chromatography
  8. customobtaining a white solid of 10.98 g
  9. customThe white solid was recrystallized with a mixed solvent of Solumix/heptane in a ratio of 1:1

Sources & evidence

ORD record
ord-db407111515b436e9b76d103fe58f539
Source dataset
uspto-grants-2010_09
Patent number
US07790915B2

Reaction notes

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