Sodium Benzoate → (3,5-Dichloro-2,6-difluoropyridin-4-yl)methyl benzoate

HRID 426298Notes

Reaction equation

HRID 426298 reaction equation
Br[CH2:2][C:3]1[C:8]([Cl: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>[C:13]([O:21][CH2:2][C:3]1[C:8]([Cl:9])=[C:7]([F:10])[N:6]=[C:5]([F:11])[C:4]=1[Cl:12])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 517055Sodium BenzoateHCID 591847064-(Bromomethyl)-3,5-dichloro-2,6-difluoropyridine

Product 1

HCID 59184839(3,5-Dichloro-2,6-difluoropyridin-4-yl)methyl benzoateYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred DMF (90 ml) in an ice bath, 4-(bromomethyl)-3,5-dichloro-2,6-difluoropyridine (20 g, 72 mmol) and sodium benzoate (15 g, 104 mmol) were added. After 1 hr., the mixture was stirred in a water bath for ca. 20 hr. The product was then extracted with ether, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a light brown oil. The light brown oil was purified by silica gel column chromatography (eluent, ether:hexane (1:15) to afford 18.6 g (81%) of (3,5-dichloro-2,6-difluoropyridin-4-yl)methyl benzoate as a colorless oil. 1H NMR (200 MHz, CDCl3) δ 5.61 (2H, s), 7.40-7.64 (3H, m), 8.00-8.05 (2H, m).

Workup

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

Sources & evidence

ORD record
ord-af5300de0bd24263a6c66477c2980d15
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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