Cesium carbonate → HCID 59610024, compound

HRID 1889166Notes

Reaction equation

HRID 1889166 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:16][O:17][C:18](=[O:36])[CH:19](Br)[C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(#N)C.C(OCC)(=O)C>[CH3:16][O:17][C:18](=[O:36])[CH:19]([O:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])[C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)(=[O:27])=[O:28])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 59610060HCID 59610060, compound

Product 1

HCID 59610024HCID 59610024, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2, 4 difluorophenol (0.28 g, 2.18 mmol) and cesium carbonate (0.39 g, 1.19 mmol) in acetonitrilie (20 ml) stirred for 30 mins. A solution of bromo-[4-(tetrahydro-pyran-4-sulfonyl)-phenyl]-acetic acid methyl ester (0.75 g, 1.98 mmol) in acetonitrile (5 ml) was added drop wise at room temperature and stirred further for 2 hrs. Reaction mixture was diluted with ethyl acetate (50 ml), washed with water, 1N NaOH (cold, 50 ml), and brine (50 ml) dried over anhydrous sodium sulfate, filtered and concentrated to provide (2,4-difluoro-phenoxy)-[4-(tetrahydro-pyran-4-sulfonyl)-phenyl]-acetic acid methyl ester (0.35 gm).

Workup

  1. stirringstirred further for 2 hrs
  2. customReaction mixture
  3. washwashed with water, 1N NaOH (cold, 50 ml), and brine (50 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7d14bb2e11eb40d39a0126029f3ad53e
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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