Toluene → 7-(3-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one

HRID 1051109Notes

Reaction equation

HRID 1051109 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][CH2:14][C:15]2=[O:18])=[CH:10][CH:9]=1.[F:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=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:19][C:20]1[CH:25]=[C:24]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][CH2:14][C:15]3=[O:18])=[CH:10][CH:9]=2)[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-oneHCID 27339863-Fluorophenylboronic acid

Product 1

HCID 820844927-(3-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-oneYield 54.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Cesium carbonate (869 mg, 2.67 mmol) was added to a solution of 7-bromo-3,4-dihydronaphthalen-1(2H)-one (300 mg, 1.33 mmol), (3-fluorophenyl) boronic acid (372 mg, 2.67 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) (15 mg, 0.013 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 174 mg (54%) of 7-(3-fluorophenyl)-3,4-dihydronaphthalen-1(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-0276ac6448e54928ba131a8f9f7ec09d
Source dataset
uspto-grants-2016_07
Patent number
US09388153B2

Reaction notes

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