Sodium Benzoate → Benzoic acid 3-chloro-2,5,6-trifluoro-pyridin-4-ylmethyl ester

HRID 426226Notes

Reaction equation

HRID 426226 reaction equation
Br[CH2:2][C:3]1[C:8]([F:9])=[C:7]([F:10])[N:6]=[C:5]([F:11])[C:4]=1[Cl:12].[C:13]([O-:21])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+]>CN(C=O)C.CCOCC>[Cl:12][C:4]1[C:5]([F:11])=[N:6][C:7]([F:10])=[C:8]([F:9])[C:3]=1[CH2:2][O:21][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 517055Sodium BenzoateHCID 591848554-Bromomethyl-3-chloro-2,5,6-trifluoro-pyridine

Product 1

HCID 59184703Benzoic acid 3-chloro-2,5,6-trifluoro-pyridin-4-ylmethyl esterYield 66%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the 4-bromomethyl-3-chloro-2,5,6-trifluoro-pyridine (15.6 g, 59.9 mmol) in DMF (90 ml) cooled in an ice bath, sodium benzoate (12.9 g, 89.8 mmol) was added. After 1 hr., the mixture was stirred in a water bath for ca. 20 hr. The mixture was then diluted with ether, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a light brown oil. The crude product was purified by silica gel column chromatography (eluent, ether:hexane (1:15) to afford 11.9 g (66%) of benzoic acid 3-chloro-2,5,6-trifluoro-pyridin-4-ylmethyl ester as a white solid. m.p. 60° C.; 1H NMR (200 MHz, CDCl3) δ 5.54 (2H, d, J=1.6 Hz), 7.41-7.64 (3H, m), 8.00-8.05 (2H, m).

Workup

  1. washwashed with water twice
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto give a light brown oil
  6. customThe crude product was purified by silica gel column chromatography (eluent, ether:hexane (1:15)

Sources & evidence

ORD record
ord-ffde03b4069146deb94d7c3fb04762f7
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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