Dibromomethane → 5-Bromo-1,3-benzodioxole-4-carboxaldehyde
Reaction equation
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[C:5]([OH:11])=[CH:4][CH:3]=1.Br[CH2:13]Br.[F-].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:13][O:10][C:6]=2[C:7]=1[CH:8]=[O:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
6-Bromo-2,3-dihydroxybenzaldehyde (1.82 g, 8.39 mmol) was dissolved in DMF (20 mL) and dibromomethane (1.57 g, 9.00 mmol) and potassium fluoride (2.44 g, 42.00 mmol) were added. The reaction mixture was heated to 100° C. for 2 h at which time TLC analysis indicated the reaction complete. The reaction mixture was cooled to ambient temperature and partitioned between water and methylene chloride. The organic layers were washed 4× with water, dried with magnesium sulfate, and concentrated by rotary evaporation to afford 0.60 g of product (2.62 mmol, 31% yield) as an oil. 1H NMR (CDCl3) δ 10.24 (s, 1H), 7.09 (d, J=8.3 Hz, 1H), 6.79 (d, J=8.3 Hz, 1H), 6.10 (s, 2H).
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- custompartitioned between water and methylene chloride
- washThe organic layers were washed 4× with water
- dry with materialdried with magnesium sulfate
- concentrationconcentrated by rotary evaporation
Sources & evidence
- ORD record
- ord-9e78c3dd56bd40549aa7001298e78b96
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05948817
Reaction notes
Loading…