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

HRID 25746

반응식

HRID 25746 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O>COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 114661-Bromo-4-nitrobenzeneHCID 27339582-Methoxyphenylboronic acid

생성물 1

HCID 131434782-Methoxy-4'-nitro-1,1'-biphenyl수율 72.4%

시약·촉매·용매 2

HCID 80711,2-Dimethoxyethane용매HCID 10340Sodium Carbonate용매

반응 조건

온도
120 °C

실험 절차

A mixture of 20.8 g of 4-bromonitrobenzene and 17.2 g of 2-methoxyphenyl boronic acid in 340 mL of ethylene glycol dimethyl ether and 170 mL of 2 M sodium carbonate solution was purged with argon gas and then 3.6 g of Pd(PPh3)2Cl2 was added under argon atmosphere. The reaction mixture was heated in a sealed flask at 120° C. overnight. The reaction mixture was cooled down to room temperature. The mixture was filtered through diatomaceous earth and the filtrate was diluted with water and the product was extracted three times with EtOAc. The organic layers were combined, dried over magnesium sulfate (MgSO4), and the solvent was evaporated in vacuo. The residue was purified by flash chromatography to yield 17.1 g of 2-methoxy-4′-nitrobiphenyl as a solid.

후처리

  1. customwas purged with argon gas
  2. addition3.6 g of Pd(PPh3)2Cl2 was added under argon atmosphere
  3. temperatureThe reaction mixture was cooled down to room temperature
  4. filtrationThe mixture was filtered through diatomaceous earth
  5. additionthe filtrate was diluted with water
  6. extractionthe product was extracted three times with EtOAc
  7. dry with materialdried over magnesium sulfate (MgSO4)
  8. customthe solvent was evaporated in vacuo
  9. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-6e5a00daa6644cc593f8f07d843498b7
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858627B2

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