Potassium Carbonate → HCID 22475204, compound

HRID 2103133Notes

Reaction equation

HRID 2103133 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([F:9])[CH:3]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[C:13]([F:20])[CH:12]=1.[C:21](=O)([O-])[O-:22].[K+].[K+].[C]=O>C1(OC)C=CC=CC=1.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.C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:21]([C:14]2[CH:15]=[CH:16][C:11]([Br:10])=[CH:12][C:13]=2[F:20])=[O:22])=[C:4]([F:9])[CH:3]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 27245164-Bromo-2-fluoro-1-iodobenzeneHCID 27733334-Bromo-2-fluorobenzeneboronic acidHCID 178418416HCID 178418416, compound

Product 1

HCID 22475204HCID 22475204, compoundYield 47.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 7519AnisoleSolvent2×HCID 22272177Toluene waterSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0.15 g, 0.13 mmol) was dissolved in anisole (15 mL). 1-Bromo-3-fluoro-4-iodobenzene (2.0 g, 6.6 mmol), 4-bromo-2-fluorobenzeneboronic acid (1.45 g, 6.6 mmol) and potassium carbonate (2.7 g, 19.9 mmol) together with another 15 mL anisole were added. The above mixture was stirred for 16 h at 80° C. under 10 bar carbon monoxide pressure. The reaction mixture was allowed to cool, added to a toluene/water mixture (120 mL, 1:1) the phases were separated and the water phase was extracted twice with toluene. Organic phases were pooled, washed with brine and the solvent was evaporated. Crystallization from hexane afforded the title compound as white crystals (1.17 g, 47%).

Workup

  1. temperatureto cool
  2. customwere separated
  3. extractionthe water phase was extracted twice with toluene
  4. washwashed with brine
  5. customthe solvent was evaporated
  6. customCrystallization from hexane

Sources & evidence

ORD record
ord-836f4adff1214b8894dd6c8ef1615b4b
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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