Benzyl 2-(3,5-dichloro-2,6-difluoropyridin-4-yl)acetate → 3,5-Dichloro-2,6-difluoro-4-pyridineacetic acid

HRID 426296Notes

Reaction equation

HRID 426296 reaction equation
[Cl:1][C:2]1[C:3]([F:21])=[N:4][C:5]([F:20])=[C:6]([Cl:19])[C:7]=1[CH2:8][C:9]([O:11]CC1C=CC=CC=1)=[O:10]>[Pd].C(O)C>[Cl:19][C:6]1[C:5]([F:20])=[N:4][C:3]([F:21])=[C:2]([Cl:1])[C:7]=1[CH2:8][C:9]([OH:11])=[O:10]

Participants

4

Reactant 1

HCID 59184758Benzyl 2-(3,5-dichloro-2,6-difluoropyridin-4-yl)acetate

Product 1

HCID 591847703,5-Dichloro-2,6-difluoro-4-pyridineacetic acidYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 2-(3,5-dichloro-2,6-difluoropyridin-4-yl)acetate (30.9 g, 93 mmol), anhydrous ethanol, and 10% palladium on carbon were placed into a 500 mL bottle. The mixture was then hydrogenated using Parr Hydrogenator under hydrogen atmosphere (20 psi) for 30 min. The reaction mixture was then filtered through celite pad and the pad was washed with ethanol. The filtrate was evaporated in vacuo and the residue was recrystallized from MC to afford 21 g (89%) of 2-(3,5-dichloro-2,6-difluoropyridin-4-yl)acetic acid as a white solid. m.p. 157-159° C. 1H NMR (200 MHz, CDCl3) δ 4.13 (2H, s).

Workup

  1. customfor 30 min
  2. filtrationThe reaction mixture was then filtered through celite pad
  3. washthe pad was washed with ethanol
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was recrystallized from MC

Sources & evidence

ORD record
ord-36ec8a70541d4d33a01a91cbe50dbf25
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

Loading…