Potassium Carbonate → HCID 23005147, compound

HRID 1669243Notes

Reaction equation

HRID 1669243 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(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:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66312p-BromopropiophenoneHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 23005147HCID 23005147, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

To a solution of 1-(4-bromophenyl)propan-1-one (10 g, 46.9 mmol) in toluene/ethanol (47/47 ml) is added 4-trifluoromethylphenylboronic acid (10.63 g, 51.6 mmol), tetrakis(triphenylphosphine)palladium (2.7 g, 2.3 mmol), and 2 N potassium carbonate (47 mL). The reaction mixture is heated at reflux overnight, cooled to rt, and partitioned between ethyl acetate and water. The organic layer is dried and concentrated, then loaded onto silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 60% giving 1-(4′-trifluoromethylbiphenyl-4-yl)propan-1-one (11.52 g).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux overnight
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. washeluted

Sources & evidence

ORD record
ord-a4d44f7cffb043a09305580f849b34cd
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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