1-Bromo-2-nitrobenzene → 4'-Methyl-2-nitro-1,1'-biphenyl

HRID 257250

반응식

HRID 257250 반응식
C[Sn](C)(C)[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].[OH-].[K+]>CN(C=O)C.[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N+:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1)([O-:21])=[O:20]

참가 물질

7

반응물 3

HCID 113411-Bromo-2-nitrobenzeneHCID 14797Potassium HydroxideHCID 617834Stannane, trimethyl(4-methylphenyl)-

생성물 1

HCID 104431944'-Methyl-2-nitro-1,1'-biphenyl수율 90%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

A solution of 5.0 g (19.6 mmol) 4-(trimethylstannyl)toluene, 4.08 g (20.2 mmol) 1-bromo-2-nitrobenzene, and 138 mg (0.2 mmol) bis(triphenylphosphine)palladium(II) chloride in 100 mL DMF was heated to 110° C. for 4 hours. The mixture was cooled to room temperature, was poured into a mixture of brine and 1N KOH, then was extracted 3 times with ether. The combined organic material was washed with 1N KOH, was washed with brine, was dried over magnesium sulfate, was stripped of solvent in vacuo, and was chromatographed on silica gel under medium pressure using 5% ethyl acetate in hexanes to give 3.76 g (90% yield) of the title compound as a light lemon-yellow colored oil. Rf 0.31 in 10% EtOAc/hexane, visualized by UV and ammonium molybdate/ceric sulfate stain.

후처리

  1. extractionwas extracted 3 times with ether
  2. washThe combined organic material was washed with 1N KOH
  3. washwas washed with brine
  4. dry with materialwas dried over magnesium sulfate
  5. customwas chromatographed on silica gel under medium pressure

출처 및 근거

ORD 기록
ord-17845e8d170b4f5da9badba8d0bdeeb6
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05260285

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