Water → 7-Bromo-1,3-dioxaindane-5-carbaldehyde

HRID 460311

Reaction equation

HRID 460311 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6].[F-].[K+].Br[CH2:15]Br.O>CN(C=O)C>[Br:1][C:2]1[C:9]2[O:10][CH2:15][O:11][C:8]=2[CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3024DibromomethaneHCID 854055-Bromo-3,4-dihydroxybenzaldehydeHCID 522689Potassium Fluoride

Product 1

HCID 23202437-Bromo-1,3-dioxaindane-5-carbaldehydeYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 3-bromo-4,5-dihydroxy-benzaldehyde (1.52 g, 7.02 mmol) in DMF (20 mL), were added KF (4.077 g, 70.18 mmol) followed by dibromomethane (1 mL, 14.04 mmol) and the mixture heated at 140° C. for 4 hours. The solution was cooled to room temperature, water was added and the mixture extracted with ether. The organic layer was further washed with saturated aqueous NaHCO3, dried (MgSO4), filtered and evaporated to give 973 mg of 7-bromo-benzo[1,3]dioxole-5-carbaldehyde. 1H NMR (300 MHz; CDCl3): δ 6.16 (s, 2H), 7.26 (s, 1H), 7.54 (s, 1H), 9.76

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionthe mixture extracted with ether
  3. washThe organic layer was further washed with saturated aqueous NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0d38999cde49444faa0534a1045bfd1b
Source dataset
uspto-grants-2007_03
Patent number
US07196108B2

Linked notes

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