(3-Chloro-2,5,6-trifluoro-pyridin-4-yl)-acetic acid benzyl ester → (3-Chloro-2,5,6-trifluoro-pyridin-4-yl)-acetic acid

HRID 426224Notes

Reaction equation

HRID 426224 reaction equation
C([O:8][C:9](=[O:21])[CH2:10][C:11]1[C:16]([F:17])=[C:15]([F:18])[N:14]=[C:13]([F:19])[C:12]=1[Cl:20])C1C=CC=CC=1>[Pd].C1COCC1>[Cl:20][C:12]1[C:13]([F:19])=[N:14][C:15]([F:18])=[C:16]([F:17])[C:11]=1[CH2:10][C:9]([OH:21])=[O:8]

Participants

4

Reactant 1

HCID 59184738(3-Chloro-2,5,6-trifluoro-pyridin-4-yl)-acetic acid benzyl ester

Product 1

HCID 23118969(3-Chloro-2,5,6-trifluoro-pyridin-4-yl)-acetic acidYield 78.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3-chloro-2,5,6-trifluoro-pyridin-4-yl)-acetic acid benzyl ester (29 g, 91.86 mmol), anhydrous THF (180 ml), and 10% palladium on carbon (1 g) was stirred for 4 hr. at room temperature under hydrogen atmosphere. The reaction mixture was then filtered through celite pad and the pad was washed with ethanol. The combined filtrate was evaporated in vacuo and the residue was recrystallized from dichloromethane to afford 16.2 g (78%) of (3-chloro-2,5,6-trifluoro-pyridin-4-yl)-acetic acid as a white solid. m.p. 127-129° C.: 1H NMR (200 MHz, CDCl3) δ 3.97 (2H, d, J=1.6 Hz), 8.50 (1H, br. s).

Workup

  1. customat room temperature
  2. filtrationThe reaction mixture was then filtered through celite pad
  3. washthe pad was washed with ethanol
  4. customThe combined filtrate was evaporated in vacuo
  5. customthe residue was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-b8affaf97ea74f478ac2a4a4e14b82f4
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

Loading…