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

HRID 2120238

반응식

HRID 2120238 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6f61e9f503924afaa8e686c132437d02
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06689806B1

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