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

HRID 1060002

反応式

HRID 1060002 の反応式
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

参加物

7

反応物 3

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

生成物 1

HCID 186310034-(4-Methoxypyridin-2-yl)-2-nitrotoluene収率 95.1%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-095fc507c68f4166bbaf3abdc528761d
出典データセット
uspto-grants-2003_02
特許番号
US06521643B1

関連ノート

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