Potassium Carbonate → 2-(4'-Chloro-2,3'-difluorobiphenyl-4-yl)naphthalene

HRID 1712192Notes

Reaction equation

HRID 1712192 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1I.[Cl:19][C:20]1[CH:25]=[CH:24][C:23](OB(O)O)=[CH:22][C:21]=1[F:30].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.O.C(O)C>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:7]2[CH:6]=[CH:5][C:4]([C:9]3[CH:18]=[CH:17][C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:10]=3)=[CH:3][C:2]=2[F:1])=[CH:22][C:21]=1[F:30]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 217083164-Chloro-3-fluorophenylboric acidHCID 686168932-(3-Fluoro-4-iodophenyl)naphthalene

Product 1

HCID 588276562-(4'-Chloro-2,3'-difluorobiphenyl-4-yl)naphthalene

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

A mixture of 6.66 g (19.13 mmol) of the above-obtained 2-(3-fluoro-4-iodophenyl)naphthalene, 4.00 g (22.94 mmol) of 4-chloro-3-fluorophenylboric acid, 3.97 g (=28.72 mmol) of potassium carbonate, 1.54 g (=4.78 mmol) of tetrabutylammonium bromide, 0.40 g (=0.57 mmol) of dichlorobis(triphenylphosphine)palladium(II), 0.31 g (=1.16 mmol) of triphenylphosphine and a 60 ml mixed solvent of toluene/water/ethanol in a ratio of 1:1:1 was stirred for 44 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 yellowish solid of 9.66 g was purified with silica gel chromatography using heptane/toluene in a ratio of 5:1 as the eluent to obtain a white solid of 7.11 g, which was recrystallized with a mixed solvent of heptane/toluene in a ratio of 8:1 to obtain a product in an amount of 4.79 g, which was characterized as the target compound based on results of various instrumental analyses. The phase transitions of the product are notated as “C 121.9 N 128.7 I”.

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 yellowish solid of 9.66 g was purified with silica gel chromatography
  8. customto obtain a white solid of 7.11 g, which
  9. customwas recrystallized with a mixed solvent of heptane/toluene in a ratio of 8:1
  10. customto obtain a product in an amount of 4.79 g, which
  11. customon results of various instrumental analyses

Sources & evidence

ORD record
ord-07636b39a3644319843fdb3ebdbbdae3
Source dataset
uspto-grants-2010_09
Patent number
US07790915B2

Reaction notes

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