Potassium Carbonate → (4'-Bromo-2,3,2'-trifluorobiphenyl-4-yl)trimethylsilane

HRID 507897Notes

Reaction equation

HRID 507897 reaction equation
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11](I)=[C:10]([F:15])[CH:9]=1.[F:16][C:17]1[C:22]([F:23])=[C:21]([Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:20]=[CH:19][C:18]=1B1OCC(C)(C)CO1>O.O1CCOCC1.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:7][C:8]1[CH:13]=[CH:12][C:11]([C:18]2[CH:19]=[CH:20][C:21]([Si:24]([CH3:25])([CH3:27])[CH3:26])=[C:22]([F:23])[C:17]=2[F:16])=[C:10]([F:15])[CH:9]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27245164-Bromo-2-fluoro-1-iodobenzeneHCID 108918462-(2,3-Difluoro-4-trimethylsilylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane

Product 1

HCID 11462508(4'-Bromo-2,3,2'-trifluorobiphenyl-4-yl)trimethylsilaneYield 88%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 16.6 g (120 mmol) of K2CO3 in 50 ml of water is added to a solution of 15 g (50 mmol) of 4-bromo-2-fluoro-1-iodobenzene, 14.9 g (50 mmol) of 6 and 2.31 g (2 mmol) of [Pd(PPh3)4] in 100 ml of dioxane, and the mixture is refluxed overnight. The organic phase is washed with water and sat. NaCl, dried over MgSO4 and filtered through SiO2. The solvent is removed under reduced pressure, petroleum ether is added to the oily residue, and the product is recrystallised at −25° C. (yield: 88%, m.p. 78.0° C.).

Workup

  1. temperaturethe mixture is refluxed overnight
  2. washThe organic phase is washed with water and sat. NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered through SiO2
  5. customThe solvent is removed under reduced pressure, petroleum ether
  6. additionis added to the oily residue
  7. customthe product is recrystallised at −25° C. (yield: 88%, m.p. 78.0° C.)

Sources & evidence

ORD record
ord-e46f8500c24d47c0844bf9e6ed505d19
Source dataset
uspto-grants-2010_08
Patent number
US07786332B2

Reaction notes

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