Toluene → 6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-one

HRID 1051093Notes

Reaction equation

HRID 1051093 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][CH2:13][C:14]2=[O:17])=[CH:10][CH:9]=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:16]=[C:15]3[C:11]([CH2:12][CH2:13][C:14]3=[O:17])=[CH:10][CH:9]=2)[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 1397781-Indanone, 6-bromo-HCID 27339863-Fluorophenylboronic acid

Product 1

HCID 820809706-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-oneYield 81.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Cesium carbonate (618 mg, 1.90 mmol) was added to a solution of 6-bromo-2,3-dihydro-1H-inden-1-one (200 mg, 0.948 mmol), (3-fluorophenyl)boronic acid (265 mg, 1.90 mmol) and toluene (20 mL) in a 50 mL Schlenk tube at room temperature. A nitrogen atmosphere was established by evacuating and refilling with nitrogen (3×), then tetrakis(triphenylphosphine)palladium (0) (11 mg, 0.001 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 in vacuo. The resulting crude residue was purified on a Teledyne-Isco combiflash machine (40 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 174 mg (81%) of 6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-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 in vacuo
  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-d52ee3dc9e704853b4ae989e614d9f7a
Source dataset
uspto-grants-2016_07
Patent number
US09388153B2

Reaction notes

Loading…