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

HRID 404126노트

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HRID 404126 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d6e06d9e0cc64d1480582a0351d5e438
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748426B2

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