Bromine → 5-Bromo-2-hydroxy-4-methoxybenzaldehyde

HRID 396593

Reaction equation

HRID 396593 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>ClCCl.CCOC(C)=O>[Br:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:2]([OH:1])=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

5

Reactant 2

HCID 24408BromineHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 8181085-Bromo-2-hydroxy-4-methoxybenzaldehydeYield 84.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Ex-62A: A solution of 2-hydroxy-4-methoxybenzaldehyde (3.03 g, 20 mmol) in 25 mL of dichloromethane was cooled to 0° C. and treated dropwise with a solution of bromine (3.41 g, 21 mmol) in 10 mL of dichloromethane. The reaction mixture was stirred at 0° C. for 1.5 hours. The solvent was removed by rotary evaporation to give a residue. The residue was taken up in EtOAc and washed with 3 portions of water. The organic layer was dried over MgSO4. The drying agent was removed by filtration, and solvent was removed by rotary evaporation to give 3.9 g of the desired 5-bromo-2-hydroxy-4-methoxybenzaldehyde as a solid, m.p. 111-115° C.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customto give a residue
  3. washwashed with 3 portions of water
  4. dry with materialThe organic layer was dried over MgSO4
  5. customThe drying agent was removed by filtration, and solvent
  6. customwas removed by rotary evaporation

Sources & evidence

ORD record
ord-e385bc02cc6c425bae57c8d05128fab0
Source dataset
uspto-grants-2003_08
Patent number
US06608101B1

Linked notes

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