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

HRID 1059959

反応式

HRID 1059959 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][CH:14]=[CH:13][C:12]=1B(O)O.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:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH3:10])[CH:7]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 47384842-Bromo-4-methoxypyridine

生成物 1

HCID 186675602-(4-Methoxypyridin-2-yl)toluene収率 99.4%

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 (1.88 g), 2-methylphenylboronic acid (1.77 g) and tetrakis(triphenylphosphine)-palladium (578 mg) in 1,2-dimethoxyethane (30 ml) was added 2M aqueous solution of sodium carbonate (13 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. The residue was purified by column chromatography (silica gel 50 g, 25% ethyl acetate in n-hexane) to give 2-(4-methoxypyridin-2-yl)toluene (1.98 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. customThe residue was purified by column chromatography (silica gel 50 g, 25% ethyl acetate in n-hexane)

出典と根拠

ORDレコード
ord-a305d08f1e5542e1b07a3b2fb5615217
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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