Water → HCID 70979744, compound

HRID 1468662Notes

Reaction equation

HRID 1468662 reaction equation
Cl[CH2:2][C:3]([CH3:5])=[O:4].[F:6][C:7]1[CH:8]=[C:9]([OH:17])[CH:10]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:6][C:7]1[CH:8]=[C:9]([CH:10]=[C:11]([S:13]([CH3:16])(=[O:14])=[O:15])[CH:12]=1)[O:17][CH2:2][C:3](=[O:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 84662442HCID 84662442, compound

Product 1

HCID 70979744HCID 70979744, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

1-Chloroacetone (95%, 2.66 g, 27.34 mmol) was added to a stirred solution of 3-fluoro-5-methylsulfonyl-phenol (80%, 1.3 g, 5.46 mmol) and potassium carbonate (2.26 g, 16.40 mmol) in dry dimethyl formamide (10 ml), the mixture was heated to 120° C. for 20 minutes, the mixture was allowed to cool to ambient temperature and water (100 ml) was added. The aqueous phase was extracted with ethyl acetate (3×100 ml), the combined organic phase was washed with LiCl (5% aqueous solution, 4×50 ml), brine (50 ml) and dried with Na2SO4 and evaporated. Purification on flash chromatography (isooctane: ethyl acetate 1:0 to 3:2). 0.905 g, 67%. MS m/z (relative intensity, 70 eV) 246 (M+, 79), 204 (55), 203 (bp), 141 (30), 94 (67).

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×100 ml)
  3. washthe combined organic phase was washed with LiCl (5% aqueous solution, 4×50 ml), brine (50 ml)
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customPurification on flash chromatography (isooctane: ethyl acetate 1:0 to 3:2)

Sources & evidence

ORD record
ord-3183b66287e24761ad03a651a33389ac
Source dataset
uspto-grants-2015_04
Patent number
US09006227B2

Reaction notes

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