Bromine → 4-Bromo-7-methoxy-1-benzofuran-2-carbaldehyde

HRID 1108316Notes

Reaction equation

HRID 1108316 reaction equation
[CH:1]([C:3]1[O:4][C:5]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1)=[O:2].C([O-])(=O)C.[Na+].[Br:19]Br>ClCCl>[CH:1]([C:3]1[O:4][C:5]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]([Br:19])[C:6]=2[CH:7]=1)=[O:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 34573107-Methoxy-1-benzofuran-2-carbaldehyde

Product 1

HCID 187848644-Bromo-7-methoxy-1-benzofuran-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-Formyl-7-methoxybenzofuran (1.0 g) was stirred in dichloromethane (10 ml) under nitrogen at 0° C. Sodium acetate (1.4 g) was added followed by the dropwise addition of bromine (0.29 ml). Further dichloromethane (20 ml) was added to the mixture to facilitate stirring and the mixture was stirred overnight. The reaction mixture was diluted with dichloromethane (40 ml) and washed with water (30 ml). Drying over magnesium sulfate followed by removal of the solvent in vacuo gave a pale orange solid. Purification by flash chromatography on silica eluting with 10% ethyl acetate in hexane gave the title compound (0.50 g) as a beige solid.

Workup

  1. stirringthe mixture was stirred overnight
  2. washwashed with water (30 ml)
  3. dry with materialDrying over magnesium sulfate
  4. customfollowed by removal of the solvent in vacuo
  5. customgave a pale orange solid
  6. customPurification by flash chromatography on silica eluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7eb9a6b965734d07987a37983b422353
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

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