Potassium Carbonate → HCID 22723462, compound

HRID 1581786Notes

Reaction equation

HRID 1581786 reaction equation
O1CCOCC1.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1B(O)O.Br[C:20]1[S:21][CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[S:21]1[CH:22]=[CH:23][CH:24]=[C:20]1[C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][CH3:7]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 138512-BromothiopheneHCID 312751,4-DioxaneHCID 27826735-Fluoro-2-methoxyphenylboronic acid

Product 1

HCID 22723462HCID 22723462, compoundYield 243.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To dioxane (113 ml) is added 2-methoxy-5-fluorophenylboronic acid (4.25 g, 24.9 mmol), 2-bromothiophene (3.65 g, 22.7 mmol, 0.9 eq.) and potassium carbonate (2M, 37 ml). Palladium (0) tetrakistriphenylphoshine (0.03 eq.) is then added and the resulting mixture is heated to 85° C. for 3 hours. The reaction is cooled to room temperature and poured into ethyl acetate and water. The aqueous layer is extracted twice with ethyl acetate. The organic layers are combined, and dried over sodium sulfate, concentrated to a brown oil and the resulting residue is flash chromatographed in 20% toluene/hexanes to afford 11.5 g of 2-(thien-2-yl)-4-fluoroanisole (90%).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. extractionThe aqueous layer is extracted twice with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to a brown oil
  5. customchromatographed in 20% toluene/hexanes

Sources & evidence

ORD record
ord-4955e1166cb2461ba7d1c1fbc6bb17ef
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

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