3-Nitrophenylboronic Acid → HCID 18667584, 화합물

HRID 1059920

반응식

HRID 1059920 반응식
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[N+:10]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)([O-:12])=[O:11].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.ClCCl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:17]2[CH:18]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=[CH:15][CH:16]=2)[CH:7]=1

참가 물질

7

반응물 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 47384842-Bromo-4-methoxypyridine

생성물 1

HCID 18667584HCID 18667584, 화합물수율 61.7%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6344Dichloromethane용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

To a suspension of 2-bromo-4-methoxypyridine (483 mg), 3-nitrophenylboronic acid (643 mg) and tetrakis(triphenylphosphine)-palladium (148 mg) in 1,2-dimethoxyethane (10 ml) was added 2M aqueous solution of sodium carbonate (2.78 ml). The mixture was stirred at 90° C. for 6 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with dichloromethane. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 40 g, 50-100% dichloromethane in n-hexane) to give 3-(4-methoxypyridin-2-yl)-nitrobenzene (365 mg).

후처리

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 40 g, 50-100% dichloromethane in n-hexane)

출처 및 근거

ORD 기록
ord-717226425c9d4f4e9fbc40d41e0a04bb
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521643B1

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