1,2-Dibromoethane → 8-Fluoro-2,3-dihydro-1,4-benzodioxin-6-carboxaldehyde

HRID 15308

Reaction equation

HRID 15308 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20]Br>CN(C=O)C>[F:1][C:2]1[C:9]2[O:10][CH2:19][CH2:20][O:11][C:8]=2[CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 5936643-Fluoro-4,5-dihydroxybenzaldehyde

Product 1

HCID 574231098-Fluoro-2,3-dihydro-1,4-benzodioxin-6-carboxaldehydeYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-fluoro-4,5-dihydroxybenzaldehyde (0.66 g, 4.2 mmol) in DMF (30 ml) was added potassium carbonate (1.15 g, 8.3 mmol) and 1,2-dibromoethane (0.72 ml, 8.3 mmol) and the resultant mixture was heated to 80° C. for 18 h before the solvent was removed under reduced pressure. The reaction mixture was then treated with dichloromethane and water. The aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried and the solvent was removed under reduced pressure to give the desired compound as a cream solid (0.73 g, 95%).

Workup

  1. customwas removed under reduced pressure
  2. additionThe reaction mixture was then treated with dichloromethane and water
  3. extractionThe aqueous phase was extracted twice with dichloromethane
  4. customthe combined organic phases were dried
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ae2de73b0a5c4c679f9b21e0b468d267
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Linked notes

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