Water → 4-(2,2-Dimethyl-4-oxo-4H-benzo[1,3]dioxin-7-yloxy)-3,5-difluoro-benzaldehyde

HRID 1436320Notes

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]=[C:22]([F:25])[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[C:16]([F:15])=[CH:17][C:18]([CH:19]=[O:20])=[CH:21][C:22]=3[F:25])=[CH:3][C:4]=2[O:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

7-Hydroxy-2,2-dimethyl-benzo[1,3]dioxin-4-one (I-1a: 12.9 g) and 3,4,5-trifluorobenzaldehyde (5.0 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 5-10% ethyl acetate in heptane to give the title compound (I-1b-2).

Workup

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

Sources & evidence

ORD record: ord-b687bdd98fc741e8ae2461e54e93865f
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618996B2

Reaction notes

Loading…