Bromochloromethane → 1,3-Benzodioxole-4-carboxaldehyde

HRID 1249945Notes

Reaction equation

HRID 1249945 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11](=O)([O-])[O-].[Cs+].[Cs+].BrCCl>C(#N)C>[CH2:11]1[O:10][C:9]2[C:2](=[C:3]([CH:6]=[CH:7][CH:8]=2)[CH:4]=[O:5])[O:1]1

Participants

5

Reactant 3

HCID 6333BromochloromethaneHCID 10796Cesium carbonateHCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 822641,3-Benzodioxole-4-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mechanically stirred degassed mixture of 2,3-dihydroxy benzaldehyde (7.80 g, 56 mmol) and cesium carbonate (16.20 g, 84 mmol) in acetonitrile (110 ml) was added bromochloromethane (5.46 g, 84 mmol) and the resulting suspention was heated to reflux. After 5 hours the reaction was cooled to room temperature and filtered through celite with ethyl acetate washings. The filtrate was concentrated and directly chromatographed on silica gel using 9:1 hexane:ethyl acetate as eluent.

Workup

  1. customdegassed
  2. temperaturethe resulting suspention was heated to reflux
  3. filtrationfiltered through celite with ethyl acetate washings
  4. concentrationThe filtrate was concentrated
  5. customdirectly chromatographed on silica gel using 9:1 hexane

Sources & evidence

ORD record
ord-fb43004556ba4c4fab7e96cd7c7b554d
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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