Potassium trimethylsilanolate → 2-(2,3-Difluoro-phenylsulfanyl)-2-methyl-propionic acid

HRID 1809390Notes

Reaction equation

HRID 1809390 reaction equation
C([O:3][C:4](=[O:17])[C:5]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=1[F:16])([CH3:7])[CH3:6])C.C[Si](C)(C)[O-].[K+]>C1COCC1>[F:16][C:10]1[C:11]([F:15])=[CH:12][CH:13]=[CH:14][C:9]=1[S:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:17])=[O:3]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 592678492-(2,3-Difluoro-phenylsulfanyl)-2-methyl-propionic acid ethyl ester

Product 1

HCID 592678882-(2,3-Difluoro-phenylsulfanyl)-2-methyl-propionic acidYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.64 g (6.31 mmol) of 2-(2,3-difluoro-phenylsulfanyl)-2-methyl-propionic acid ethyl ester in THF (165 mL) at room temperature are added 1.62 g (12.6 mmol) of potassium trimethylsilanolate. The reaction is stirred at room temperature for 18 h. The solvent is removed under reduced pressure and the residue is partitioned between water and diethyl ether. The basic aqueous layer is separated, acidified using 1M aqueous HCl solution to pH 1 and extracted with DCM (3×100 mL). The organic phase is dried over MgSO4, filtered and the filtrate is concentrated under reduced pressure to give 1.32 g of 2-(2,3-difluoro-phenylsulfanyl)-2-methyl-propionic acid as a pale yellow solid. Yield: 90%, ES-MS: m/z 231 [M−H].

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is partitioned between water and diethyl ether
  3. customThe basic aqueous layer is separated
  4. extractionextracted with DCM (3×100 mL)
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-8bc21d491038443595986ca96ebef10c
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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