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

HRID 2220268ノート

反応式

HRID 2220268 の反応式
[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

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 5359268AluminumHCID 18379633HCID 18379633、化合物HCID 53398048(6-Methyl-1-benzothiophen-2-yl)boronic acid

生成物 1

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

試薬・触媒・溶媒 4

HCID 15220664Palladium--triphenylphosphane (1/1)触媒HCID 178418397HCID 178418397、化合物触媒HCID 241Benzene溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-a9e94fbd2c8e470eb5eaf7e178d9144e
出典データセット
uspto-grants-2008_08
特許番号
US07417065B2

反応ノート

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