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

HRID 257250

反応式

HRID 257250 の反応式
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]

参加物

7

反応物 3

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

生成物 1

HCID 104431944'-Methyl-2-nitro-1,1'-biphenyl収率 90%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-17845e8d170b4f5da9badba8d0bdeeb6
出典データセット
uspto-grants-1993_11
特許番号
US05260285

関連ノート

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