Dichloromethane → (4'-Nitrobiphenyl-3,4-diyl)dimethanol

HRID 404126ノート

反応式

HRID 404126 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH2:10][OH:11])[CH:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)O1.ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[N+:26]([C:23]1[CH:24]=[CH:25][C:20]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH2:10][OH:11])[CH:3]=2)=[CH:21][CH:22]=1)([O-:28])=[O:27]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27735554,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolaneHCID 10798791(5-Bromo-2-(hydroxymethyl)phenyl)methanol

生成物 1

HCID 67306898(4'-Nitrobiphenyl-3,4-diyl)dimethanol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

The compound of example 669 (7 g, 32.25 mmol), 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (9.63 g, 38.70 mmol) and [1,1-Bis(diphenylphosphino)-ferrocine]dichloropalladium(II), complex with dichloromethane (789 mg, 0.967 mmol) were taken in dry DMF under Argon atmosphere. Degassed 2M solution of sodium carbonate (8.54 g, 80.62 mmol) was added and the reaction mixture was heated to 80° C. for 3 h. The reaction mixture was cooled and the solvent was removed by distillation. The residue was taken in water and the aqueous mixture was extracted with ethyl acetate. The crude material obtained was purified using column chromatography (silicagel, 30% dichloromethane in petroleum ether) to afford the title compound.

後処理

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed by distillation
  4. extractionthe aqueous mixture was extracted with ethyl acetate
  5. customThe crude material obtained
  6. customwas purified

出典と根拠

ORDレコード
ord-d6e06d9e0cc64d1480582a0351d5e438
出典データセット
uspto-grants-2014_06
特許番号
US08748426B2

反応ノート

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