Sodium Carbonate → 4-Methoxy-3-(thiophen-2-yl)benzaldehyde

HRID 2120238

反応式

HRID 2120238 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1Br.C(=O)([O-])[O-].[Na+].[Na+].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1B(O)O>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>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[C:19]1[S:18][CH:22]=[CH:21][CH:20]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 986623-Bromo-4-methoxybenzaldehydeHCID 27339602-Thiopheneboronic acid

生成物 1

HCID 219810244-Methoxy-3-(thiophen-2-yl)benzaldehyde収率 87%

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) (0.24 g, 0.21 mmol) was added to a solution of 4-methoxy-3-bromobenzaldehyde (1.5 g, 6.98 mmol) in toluene (15 mL) and ethanol (15 mL), followed by a 2 M aqueous solution of sodium carbonate (14 mL, 28 mmol). To this mixture was added thiophene-2-boronic acid (0.98 g, 7.68 mmol), and the mixture was heated to reflux. After 3 hours, the reaction was partitioned between water (100 mL) and ethyl acetate (250 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (75 mL) and brine (75 mL), dried with magnesium sulfate and concentrated. Chromatography (silica, 20% ethyl acetate/hexanes) afforded 1.3 g (87%) of 4-methoxy-3-thiophen-2-yl-benzaldehyde as a yellow oil.

後処理

  1. temperaturethe mixture was heated to reflux
  2. customthe reaction was partitioned between water (100 mL) and ethyl acetate (250 mL)
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate (75 mL) and brine (75 mL)
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-6f61e9f503924afaa8e686c132437d02
出典データセット
uspto-grants-2004_02
特許番号
US06689806B1

関連ノート

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