Potassium Carbonate → HCID 59363845, compound

HRID 1430646Notes

Reaction equation

HRID 1430646 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:23])[C:10](Br)([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[CH3:11].[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[OH:32]>CN(C=O)C>[CH3:7][O:8][C:9](=[O:23])[C:10]([O:32][C:26]1[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:25]=1[F:24])([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230512,4-DifluorophenolHCID 59363842HCID 59363842, compound

Product 1

HCID 59363845HCID 59363845, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Potassium carbonate (0.15 g, 1.08 mmol) was added to a mixture of 2-Bromo-2-(4-methanesulfonyl-phenyl)-propionic acid methyl ester and 2,4-difluorophenol in DMF (5 ml) and heated at 60-70° C. for 2-3 Hrs then cool the reaction mixture to RT and poured onto water (25 ml) which was then extracted with ethyl acetate (2×25 ml), organic layer was washed with water (2×25 ml), dried over sodium sulfate and solvent was removed under reduced pressure to get 2-(2,4-Difluoro-phenoxy)-2-(4-methanesulfonyl-phenyl)-propionic acid methyl ester as oil which was taken in a mixture of methanol (5 ml) and sodium hydroxide in water (0.04 g in 5 ml). This mixture was stirred at room temperature for overnight. Methanol was removed from the reaction mixture, acidified with 1N HCl, extracted with ethyl acetate (2×25 ml), washed with brine (20 ml), solvent was removed to get the desired product 2-(2,4-Difluoro-phenoxy)-2-(4-methanesulfonyl-phenyl)-propionic acid. 1H NMR (400 MHz, CDCl3): δ 1.82 (s, 3H), 3.45 (s, 3H), 6.71-6.75 (m, 1H), 6.81-6.93 (m, 2H), 7.86 (d, J=8.4 Hz, 2H), 7.95 (d, J=8.4 Hz, 2H).

Workup

  1. temperaturethen cool the reaction mixture to RT
  2. additionpoured onto water (25 ml) which
  3. extractionwas then extracted with ethyl acetate (2×25 ml), organic layer
  4. washwas washed with water (2×25 ml)
  5. dry with materialdried over sodium sulfate and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-cb66b30fc575410294c5037589e1366b
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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