Water → 4-(2,2-Dimethyl-4-oxo-4H-benzo[1,3]dioxin-7-yloxy)-3-fluoro-benzaldehyde

HRID 1436319Notes

Reaction equation

HRID 1436319 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[O:9][C:4]=2[CH:3]=1.[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1F)[CH:19]=[O:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:11][C:8]1([CH3:10])[O:7][C:6](=[O:12])[C:5]2[CH:13]=[CH:14][C:2]([O:1][C:23]3[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][C:16]=3[F:15])=[CH:3][C:4]=2[O:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5880883,4-DifluorobenzaldehydeHCID 105839507-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

Product 1

HCID 579390354-(2,2-Dimethyl-4-oxo-4H-benzo[1,3]dioxin-7-yloxy)-3-fluoro-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

7-Hydroxy-2,2-dimethyl-benzo[1,3]dioxin-4-one (I-1a: 12.9 g), 3,4-difluorobenzaldehyde (9.45 g) and potassium carbonate (27.6 g) were combined in dimethylformamide (100 mL) and stirred as the reaction mixture was heated to 80° C. After 24 hours, the reaction mixture was cooled to ambient temperature, combined with water, and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered, and evaporated. The residue was purified by column chromatography on silica gel eluting with 10-15% ethyl acetate in heptane to give the title compound (I-1b-1).

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with 10-15% ethyl acetate in heptane

Sources & evidence

ORD record
ord-1ac1aca6bdb044c794abc45172242297
Source dataset
uspto-grants-2009_11
Patent number
US07618996B2

Reaction notes

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