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

HRID 1765413Notes

Reaction equation

HRID 1765413 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-e045b9fc83f04f16ac10b06b73ef59eb
Source dataset
uspto-grants-2007_06
Patent number
US07226940B2

Reaction notes

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