Sodium Carbonate → 4-(4-Trifluoromethylphenyl)-1-indanone

HRID 1595246

반응식

HRID 1595246 반응식
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[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-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)C>[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH2:5][C:6]3=[O:11])=[CH:16][CH:15]=1

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 987131-Indanone, 4-bromo-HCID 27343894-(Trifluoromethyl)phenylboronic acid

생성물 1

HCID 217020674-(4-Trifluoromethylphenyl)-1-indanone

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매

실험 절차

6.33 g (0.03 mol) of 4-bromo-1-indanone and 5.7 g (0.03 mol) of 4-trifluoromethylphenylboronic acid are suspended with 6.36 g (0.06 mol) of sodium carbonate in a mixture of 100 ml of toluene with 20 ml of ethanol and 20 ml of water. Under an argon atmosphere, 320 mg (1.42 mmol) of palladium(II) acetate and 787 mg (3 mmol) of triphenylphosphine are added, and the mixture is boiled under reflux for 5 h. After the reaction is complete, the ethanol content is evaporated off in vacuo, 50 ml of 0.5 N sodium hydroxide solution are added to the residue, and the mixture is stirred and filtered with suction through a clarifying layer. The organic phase of the filtrate is separated off, shaken 3× with 50 ml of water each time, shaken once with saturated brine, dried over sodium sulfate and concentrated in vacuo. The crude product is chromatographed on silica gel with n-heptane/ethyl acetate 3/1. 4-(4-Trifluoromethylphenyl)-1-indanone is obtained with a melting point of 75-78° C.

후처리

  1. temperatureunder reflux for 5 h
  2. customthe ethanol content is evaporated off in vacuo, 50 ml of 0.5 N sodium hydroxide solution
  3. additionare added to the residue
  4. filtrationfiltered with suction through a clarifying layer
  5. customThe organic phase of the filtrate is separated off
  6. stirringshaken 3× with 50 ml of water each time
  7. stirringshaken once with saturated brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe crude product is chromatographed on silica gel with n-heptane/ethyl acetate 3/1

출처 및 근거

ORD 기록
ord-732508b6a1c24909a06c43ca81f0b3c7
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288094B1

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