Hydrochloric Acid → 6,7-Difluoro-5-hydroxy-2-methylbenzofuran-4-carbaldehyde

HRID 2244848Notes

Reaction equation

HRID 2244848 reaction equation
[F:1][C:2]1[C:3]([F:21])=[C:4]2[O:8][C:7]([CH3:9])=[CH:6][C:5]2=[C:10]([CH:19]=[O:20])[C:11]=1[O:12]COCCOC.Cl>C1COCC1.CC(OC)(C)C>[F:1][C:2]1[C:3]([F:21])=[C:4]2[O:8][C:7]([CH3:9])=[CH:6][C:5]2=[C:10]([CH:19]=[O:20])[C:11]=1[OH:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 592152636,7-Difluoro-5-(2-methoxyethoxymethoxy)-2-methylbenzofuran-4-carbaldehyde

Product 1

HCID 592152776,7-Difluoro-5-hydroxy-2-methylbenzofuran-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

18.0 g (60.0 mmol) of 6,7-difluoro-5-(2-methoxyethoxymethoxy)-2-methylbenzofuran-4-carbaldehyde are stirred for 17 h at 20° C. together with 11.0 ml of conc. HCl in 100 ml of THF. The reaction soln. is diluted with MTBE and washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed successively with water and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is purified by column chromatography (SiO2, 1-chlorobutane), giving 6,7-difluoro-5-hydroxy-2-methylbenzofuran-4-carbaldehyde as a yellow crystalline solid.

Workup

  1. washwashed with water
  2. extractionThe aqueous phase is extracted with MTBE
  3. washthe combined organic phases are washed successively with water and sat. sodium chloride soln
  4. customThe solution is dried
  5. concentrationconcentrated to dryness
  6. customThe crude product is purified by column chromatography (SiO2, 1-chlorobutane)

Sources & evidence

ORD record
ord-a5492903e27e43e483399335981db464
Source dataset
uspto-grants-2010_03
Patent number
US07678929B2

Reaction notes

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