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

HRID 488820

反応式

HRID 488820 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 8181085-Bromo-2-hydroxy-4-methoxybenzaldehyde収率 76%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-a692d051ed1c49f5bacadf4cbb5235bd
出典データセット
uspto-grants-2005_12
特許番号
US06974826B2

関連ノート

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