Potassium Hydroxide → 3-Bromo-1-benzofuran-5-carbaldehyde

HRID 735942Notes

Reaction equation

HRID 735942 reaction equation
Br[CH:2]1[CH:6]([Br:7])[C:5]2[CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=[CH:11][C:4]=2[O:3]1.[OH-].[K+]>C(O)C.O>[Br:7][C:6]1[C:5]2[CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=[CH:11][C:4]=2[O:3][CH:2]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 574696642,3-Dibromo-2,3-dihydro-1-benzofuran-5-carbaldehyde

Product 1

HCID 574696633-Bromo-1-benzofuran-5-carbaldehydeYield 45%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2,3-dibromo-2,3-dihydro-1-benzofuran-5-carbaldehyde (10 g) in dry ethanol (25 mL) was added a solution of KOH in dry ethanol (14 mL) and refluxed at 70° C. for 2 h. The reaction mixture was cooled, diluted with water and extracted with EtOAc (3×50 mL). The organic layer was washed with water, brine and dried. The solvent was removed under vacuum and the residue was purified by flash chromatography (PetEther/EtOAc 99.5/0.5) to give the title compound as a pale yellow solid (3.3 g, 45%). 1H NMR (DMSO-d6, 300 MHz) δ 10.12 (s, 1H), 8.47 (s, 1H), 8.14 (d, 1H, J=1.5 Hz), 7.97 (dd, 1H, J=8.6, 1.5 Hz), 7.87 (d, 1H, J=8.6 Hz).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. customThe solvent was removed under vacuum
  6. customthe residue was purified by flash chromatography (PetEther/EtOAc 99.5/0.5)

Sources & evidence

ORD record
ord-6d0fd5763d9d4d39a3ded1105e370e21
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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