2,4-Difluorophenol → 2-(2,4-Difluorophenoxy)acetic Acid 2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one-2yl Ester

HRID 1602519Notes

Reaction equation

FC1C=C(F)C=CC=1[OH:9].[F:10][C:11]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:12]=1[O:13][C:14]1[C:15](=[O:31])[O:16][C:17]([CH3:30])([CH3:29])[C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1>ClCCl>[CH3:29][C:17]([O:16][C:15](=[O:31])[CH2:14][O:13][C:12]1[CH:32]=[CH:33][C:34]([F:36])=[CH:35][C:11]=1[F:10])([CH3:30])[C:18]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1)=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride, 60% dispersion (66 mg, 1.66 mmol), was rinsed with hexane, suspended in 7 mL of DMF and cooled to 0° C. To this suspension was added 2,4-difluorophenol (170 μL, 1.79mmol). After 5 minutes at 0° C., 2-bromoacetic acid 2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one ester (Step 1) (233 mg, 1.79 mmol) was added and the reaction mixture was stirred for 30 minutes. Dichloromethane was added and the mixture was washed with 1N HCl and the organic solvent was evaporated under vacuum. The residue was dissolved in 25% EtOAc/Et2O and washed with 1N NaOH, water (2×) brine and dried over MgSO4. After filtration and evaporation of the solvent under vacuum 470 mg of the title compound was obtained.

Workup

washSodium hydride, 60% dispersion (66 mg, 1.66 mmol), was rinsed with hexane
washthe mixture was washed with 1N HCl
customthe organic solvent was evaporated under vacuum
dissolutionThe residue was dissolved in 25% EtOAc/Et2O
washwashed with 1N NaOH, water (2×) brine
dry with materialdried over MgSO4
filtrationAfter filtration and evaporation of the solvent under vacuum 470 mg of the title compound
customwas obtained

Sources & evidence

ORD record: ord-4f7fd8ff956042faa685a4d67f4d3299
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981576

Reaction notes

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