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

HRID 2228648노트

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HRID 2228648 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a181cd352cf147818d2ec63bbeb70432
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06417222B1

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