Water → HCID 86625714, compound

HRID 1662732Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:11].CC(C)([O-])C.[K+].[Br:18][C:19](Br)([F:21])[F:20].O>CN1CCN(C)C1=O>[Br:18][C:19]([F:21])([F:20])[O:11][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH3:10])[C:3]=1[O:2][CH3:1]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 5.0 g of 2,3-dimethoxy phenol in 1,3-dimethyl-2-imidazolidinone (65 ml) was added 7.28 g of potassium tert-butoxide, and was added dropwise a solution of 41.5 g of dibromo difluoromethane in 1,3-dimethyl-2-imidazolidinone (20 ml) over 30 minutes. The solution was stirred at 55° C. for 3 hours, and then water was added and the resulting mixture was extracted with Et2O. The organic layer was sequentially washed with 1 mol/L hydrochloric acid, water, and saturated brine, dried over MgSO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/9 to 1/4; v/v) to obtain 2.21 g of the title compound (colorless oil).

Workup

extractionthe resulting mixture was extracted with Et2O
washThe organic layer was sequentially washed with 1 mol/L hydrochloric acid, water, and saturated brine
dry with materialdried over MgSO4
customthe drying agent was separated by filtration
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/9 to 1/4; v/v)

Sources & evidence

ORD record: ord-25ea066572c945a7a7fec5774227ffaa
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030499B2

Reaction notes

Loading…