Sodium Carbonate → 4-(4-Methoxypyridin-2-yl)-2-nitrotoluene

HRID 1060002

반응식

HRID 1060002 반응식
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[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:14]2[CH:15]=[CH:16][C:11]([CH3:10])=[C:12]([N+:20]([O-:22])=[O:21])[CH:13]=2)[CH:7]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27735154-Methyl-3-nitrobenzeneboronic acidHCID 47384842-Bromo-4-methoxypyridine

생성물 1

HCID 186310034-(4-Methoxypyridin-2-yl)-2-nitrotoluene수율 95.1%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a suspension of 2-bromo-4-methoxypyridine (2.5 g), 4-methyl-3-nitrophenylboronic acid (3.37 g) and tetrakis(triphenylphosphine)-palladium (768 mg) in 1,2-dimethoxyethane (100 ml) was added 2M aqueous solution of sodium carbonate (18.6 ml). The mixture was stirred at 80° C. for 7 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. Methanol was added to the residue. The precipitate was collected by filtration and dried under reduced pressure to give 4-(4-methoxypyridin-2-yl)-2-nitrotoluene (3.09 g).

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. additionMethanol was added to the residue
  7. filtrationThe precipitate was collected by filtration
  8. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-095fc507c68f4166bbaf3abdc528761d
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521643B1

연결된 노트

불러오는 중…