Water → 2-Hydroxy-5-(thiophen-3-yl)benzaldehyde

HRID 2228648ノート

反応式

HRID 2228648 の反応式
Br[C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[S:11]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12]1.[F-].[Cs+].O>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.COCCOC.CO>[OH:10][C:5]1[CH:4]=[CH:3][C:2]([C:13]2[CH:14]=[CH:15][S:11][CH:12]=2)=[CH:9][C:6]=1[CH:7]=[O:8]

参加物

8

反応物 4

HCID 962WaterHCID 25953Cesium fluorideHCID 728635-BromosalicylaldehydeHCID 581760Thiophene-3-boronic acid

生成物 1

HCID 200998032-Hydroxy-5-(thiophen-3-yl)benzaldehyde

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

0.15 g of tetrakis(triphenylphosphine)palladium catalyst (1.3 10−4 mol) is added to a solution of 5-bromosalicylaldehyde (0.86 g, 0.0043 mol) and of 3-thiopheneboronic acid (0.6 g, 0.0047 mol) in 10 ml of 1,2-dimethoxyethane and 5 ml of methanol. 1.3 g of cesium fluoride are added and the mixture is heated at 80° C. for 20 hours. The reaction mixture is cooled to room temperature and poured into water. The resulting mixture is extracted with dichloromethane and the organic phase is washed with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure. The title product is isolated by chromatography on a column of silica (eluent: 88/12 cyclohexane/ethyl acetate. 0.62 g of a pale yellow solid is recovered.

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionThe resulting mixture is extracted with dichloromethane
  3. washthe organic phase is washed with saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a181cd352cf147818d2ec63bbeb70432
出典データセット
uspto-grants-2002_07
特許番号
US06417222B1

反応ノート

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