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

HRID 1595246

反応式

HRID 1595246 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-732508b6a1c24909a06c43ca81f0b3c7
出典データセット
uspto-grants-2001_09
特許番号
US06288094B1

関連ノート

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