Tetrahydrofuran → 5-(4'-Ethyl-3-fluorobiphenyl-4-yl)thiophene-2-carbaldehyde

HRID 1943515

反応式

HRID 1943515 の反応式
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20](B(O)O)=[C:19]([F:26])[CH:18]=2)=[CH:13][CH:12]=1)[CH3:10].C(=O)([O-])[O-].[Na+].[Na+].C1COCC1>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>[CH2:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:2]3[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=3)=[C:19]([F:26])[CH:18]=2)=[CH:15][CH:16]=1)[CH3:10]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 784285-Bromothiophene-2-carbaldehydeHCID 534025754'-Ethyl-3-fluorobiphenyl-4-boronic acid

生成物 1

HCID 581606825-(4'-Ethyl-3-fluorobiphenyl-4-yl)thiophene-2-carbaldehyde

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 21863594Toluene ethanol溶媒

反応条件

温度
80 °C

実験手順

A mixture of 58.5 g (0.31 mol) of 5-bromothiophene-2-carbaldehyde, 75.5 g (0.31 mol) of 4′-ethyl-3-fluoro-4-biphenylboronic acid, 17.0 g (14.7 mmol) of tetrakis(triphenylphosphine)palladium(0) and 375 ml of 2 N sodium carbonate solution in 935 ml of toluene/ethanol (1:1.5) is heated at 80° C. for 1 h. After cooling, the precipitated product is firstly dissolved by addition of THF. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride solution, and the solution is dried using sodium sulfate. The residue remaining after removal of the solvents is digested in toluene, and the product is filtered off, giving 5-(4′-ethyl-3-fluorobiphenyl-4-yl)thiophene-2-carbaldehyde as a yellow solid.

後処理

  1. temperatureAfter cooling
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is extracted with MTBE
  4. washThe combined organic phases are washed with sat. sodium chloride solution
  5. customthe solution is dried
  6. customafter removal of the solvents
  7. filtrationthe product is filtered off

出典と根拠

ORDレコード
ord-f49fa3f2b40e494593479e1b16ae875b
出典データセット
uspto-grants-2013_03
特許番号
US08394293B2

関連ノート

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