Toluene → 5-(3-fluorophenyl)benzofuran-3(2H)-one

HRID 1051114Notes

Reaction equation

HRID 1051114 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:9]=[CH:10][C:11]2[O:15][CH2:14][C:13](=[O:16])[C:12]=2[CH:17]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.C1(C)C=CC=CC=1>C(OCC)(=O)C.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>[F:18][C:19]1[CH:24]=[C:23]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH2:14][C:13](=[O:16])[C:12]=3[CH:17]=2)[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 27339863-Fluorophenylboronic acidHCID 105127485-Bromobenzo[b]furan-3(2H)-one

Product 1

HCID 1181615575-(3-fluorophenyl)benzofuran-3(2H)-oneYield 99%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Cesium carbonate (612 mg, 1.88 mmol) was added to a solution of 5-bromobenzofuran-3(2H)-one (200 mg, 0.939 mmol), (3-fluorophenyl)boronic acid (263 mg, 1.88 mmol) and toluene (20 mL) in a 50 mL Schlenk tube. A nitrogen atmosphere was established by evacuating and refilling with nitrogen (3×), then tetrakis(triphenylphosphine)palladium (0) (11 mg, 0.01 mmol) was added to the reaction. The flask was sealed and heated in a 80° C. oil bath overnight. The resulting mixture was cooled to room temperature. The reaction was then diluted with ethyl acetate and filtered through celite. Ethyl acetate (30 mL) was used to wash the flask and the combined organic filtrate was concentrated. The resulting crude residue was purified on a Teledyne-Isco Combiflash machine (40 g column, hexanes→100% ethyl acetate/hexanes, gradient), to afford 212 mg (99%) of 5-(3-fluorophenyl)benzofuran-3(2H)-one.

Workup

  1. customby evacuating
  2. customThe flask was sealed
  3. temperatureThe resulting mixture was cooled to room temperature
  4. filtrationfiltered through celite
  5. washto wash the flask
  6. concentrationthe combined organic filtrate was concentrated
  7. customThe resulting crude residue was purified on a Teledyne-Isco Combiflash machine (40 g column, hexanes→100% ethyl acetate/hexanes, gradient)

Sources & evidence

ORD record
ord-8d6a00830e8642d39928acf51cf52f8f
Source dataset
uspto-grants-2016_07
Patent number
US09388153B2

Reaction notes

Loading…