Acetone → HCID 59192522, compound

HRID 2384013Notes

Reaction equation

HRID 2384013 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10]C(O)=O)=[C:4](O)[C:3]=1[F:15].[C:16](=[O:19])([O-])[O-:17].[K+].[K+].S([O:27][CH3:28])(OC)(=O)=O.[CH3:29]C(C)=O>>[CH3:29][O:17][C:16](=[O:19])[CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:15])[C:4]=1[O:27][CH3:28]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 59192512HCID 59192512, compound

Product 1

HCID 59192522HCID 59192522, compoundYield 83%

Procedure

To a stirred solution of 4-(4-chloro-3-fluoro-2-hydroxy-phenyl)-butyric acid (6.0 g, 0.026 mol) in acetone (20 mL) was added anhydrous potassium carbonate (9.7 g, 0.07 mol) at room temperature under nitrogen. After 10 minutes, dimethyl sulfate (5.49 mL, 0.058 mol) was added and the resulting mixture was stirred for an additional 3-4 hours. The solvent was removed in vacuo and the residue was extracted with dichloromethane (25 mL×3). The combined organic layers were washed with water (15 mL×2), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 4-(4-chloro-3-fluoro-2-methoxy-phenyl)-butyric acid methyl ester (5.6 g, 83%), which was used in the next step without further purification. MS cald. for C12H14ClFO3 260, obsd. 261 [(M+H)+].

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe residue was extracted with dichloromethane (25 mL×3)
  3. washThe combined organic layers were washed with water (15 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8233dd32c8f74b2d959ea85cd0944d6f
Source dataset
uspto-grants-2012_09
Patent number
US08263656B2

Reaction notes

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