Sodium Carbonate → 2-(3-Methoxyphenyl)-4,5-dimethoxybenzaldehyde

HRID 24413

反応式

HRID 24413 の反応式
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][C:6]([CH:7]=[O:8])=[C:5](Br)[CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][O:21][C:22]1[CH:27]=[C:26]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:10]([O:11][CH3:12])=[CH:9][C:6]=2[CH:7]=[O:8])[CH:25]=[CH:24][CH:23]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 793516-Bromo-3,4-dimethoxybenzaldehydeHCID 2734370(3-Methoxyphenyl)boronic acid

生成物 1

HCID 225710312-(3-Methoxyphenyl)-4,5-dimethoxybenzaldehyde収率 98%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

Tetrakis(triphenylphosphine)palladium(0) (0.36 g) was added to a solution of 4,5-dimethoxy-2-bromobenzaldehyde (2.5 g) in toluene (20 ml) and ethanol (20 ml), followed by addition of 2M aqueous sodium carbonate (20 ml). To this mixture was added 3-methoxyphenylboronic acid (1.7 g), and the mixture was heated to reflux. After 1 hour, the reaction was partitioned between water (150 ml) and ethyl acetate (300 ml). The organic layer was washed with saturated aqueous sodium bicarbonate (150 ml) and brine (150 ml), dried over magnesium sulfate and concentrated. Chromatography (silica, 20-30-40% ethyl acetate/hexanes) afforded 2.7 g (98%) of 2-(3-methoxyphenyl)-4,5-dimethoxybenzaldehyde as a yellow oil which solidified upon standing.

後処理

  1. temperaturethe mixture was heated to reflux
  2. customthe reaction was partitioned between water (150 ml) and ethyl acetate (300 ml)
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate (150 ml) and brine (150 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-ed482061e220479d8ec3892c16a689e8
出典データセット
uspto-grants-2005_02
特許番号
US06855730B2

関連ノート

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