Water → HCID 58062997, compound

HRID 659228Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[OH:16].C(=O)([O-])[O-].[K+].[K+].Cl[C:25]([F:31])([F:30])C(OC)=O.O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C:12]([F:14])([F:13])[F:15])=[CH:6][C:5]=1[O:16][CH:25]([F:31])[F:30]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 35 mg (0.140 mmol) 2-hydroxy-6-methoxy-4-trifluoromethyl-benzoic acid methyl ester in 350 ul N,N-dimethylformamide under nitrogen at room temperature, was added 29 mg (0.210 mmol) potassium carbonate, followed dropwise by 18.1 ul (0.168 mmol) methyl chlorodifluoroacetate. The reaction mixture was heated in a 65° C. oil bath for 22 hours. Water and ethyl acetate were added. Both phases were separated and the organic layer was washed 3 times with water. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude brown oil (49 mg) was purified with flash column chromatography on silica (10 g) eluting with a gradient formed from n-heptane and ethyl acetate (0%=>10% in 15 minutes) to provide 16 mg (y: 38.1%) of the title compound as a light yellow oil.

Workup

customBoth phases were separated
washthe organic layer was washed 3 times with water
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude brown oil (49 mg) was purified with flash column chromatography on silica (10 g)
washeluting with a gradient
customformed from n-heptane and ethyl acetate (0%=>10% in 15 minutes)

Sources & evidence

ORD record: ord-38929713e1c64de29a3b9be832cd6053
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080541B2

Reaction notes

Loading…