2-Hydroxy-4-Methoxybenzaldehyde → 5-Bromo-2-hydroxy-4-methoxybenzaldehyde

HRID 488820

반응식

HRID 488820 반응식
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br-:12].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[Br:12][C:7]1[CH:6]=[C:3]([C:2]([OH:1])=[CH:9][C:8]=1[O:10][CH3:11])[CH:4]=[O:5]

참가 물질

4

반응물 2

HCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 23500184Tetra-n-butylammonium tribromide

생성물 1

HCID 8181085-Bromo-2-hydroxy-4-methoxybenzaldehyde수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-hydroxy-4-methoxy-benzaldehyde (3.04 g, 20 mmol) and tetrabutylammonium tribromide (6.40 g, 20 mmol) in anhydrous dichloromethane (200 mL) was stirred at room temperature for 24 hours. The solution was washed successively with a saturated aqueous solution of NaHCO3 (150 mL), water (150 mL), a saturated aqueous solution of NaCl (150 mL), dried over MgSO4 and filtered. Removal of the solvent under reduced pressure gave a solid which was purified by column chromatography, using a Biotage 40M cartridge, eluting with 5% ethyl acetate/95% hexane to give 3-bromo-6-hydroxy-4-methoxy-benzaldehyde as a white solid (3.50 g, 76%).

후처리

  1. washThe solution was washed successively with a saturated aqueous solution of NaHCO3 (150 mL), water (150 mL)
  2. dry with materiala saturated aqueous solution of NaCl (150 mL), dried over MgSO4
  3. filtrationfiltered
  4. customRemoval of the solvent under reduced pressure
  5. customgave a solid which
  6. customwas purified by column chromatography
  7. washeluting with 5% ethyl acetate/95% hexane

출처 및 근거

ORD 기록
ord-a692d051ed1c49f5bacadf4cbb5235bd
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06974826B2

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