Sodium Carbonate → 6-Methyl-2-[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-1-benzothiophene

HRID 2220268노트

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HRID 2220268 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8](B(O)O)[S:7][C:6]=2[CH:13]=1.Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:17]([C:27]([F:30])([F:29])[F:28])[CH:16]=1.[Al].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.[Cl-].[Na+].O.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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:17]([C:27]([F:28])([F:30])[F:29])[CH:16]=3)[S:7][C:6]=2[CH:13]=1

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 5359268AluminumHCID 18379633HCID 18379633, 화합물HCID 53398048(6-Methyl-1-benzothiophen-2-yl)boronic acid

생성물 1

HCID 684539646-Methyl-2-[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-1-benzothiophene수율 54.3%

시약·촉매·용매 4

HCID 15220664Palladium--triphenylphosphane (1/1)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 241Benzene용매HCID 57417360Sodium chloride; water용매

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온도
85 °C

실험 절차

To a slurry of 6-methyl-benzo[b]thiophene-2-boronic acid (0.19 g, 0.001 mol) in 10 mL of benzene is added 4-bromo-2-trifluoromethyl-biphenyl ( 0.3g, 0.001 mol). The reaction flask is then covered with aluminum foil to keep out light. To this is added 58 mg of tetrakis(triphenylphosphine-palladium(0), followed by 1 mL of 2.0N sodium carbonate solution. The biphasic mixture is heated at 85° C. for 3 hours with vigorous stirring. The mixture is cooled to room temperature and 10 mL of brine solution is added. The organic layer is separated, dried and concentrated under vacuo to afford 0.2g of 6-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene.

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. customThe organic layer is separated
  3. customdried
  4. concentrationconcentrated under vacuo

출처 및 근거

ORD 기록
ord-a9e94fbd2c8e470eb5eaf7e178d9144e
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417065B2

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