2,6-Difluorobenzyl alcohol → HCID 117858216, compound

HRID 1486321Notes

Reaction equation

HRID 1486321 reaction equation
F[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:12]=1[CH2:13][OH:14].CC(C)([O-])C.[K+]>O1CCCC1>[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:12]=1[CH2:13][O:14][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 879212,6-Difluorobenzyl alcoholHCID 214643612-Fluoro-4-methoxypyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 117858216HCID 117858216, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3.5 g (27.53 mmol) of 2-fluoro-4-methoxypyridine (CAS: 175965-83-0) and 3.97 g (27.53 mmol) of 2,6-difluorobenzyl alcohol in 97 ml of dry tetrahydrofuran, cooled beforehand to 0° C., were added dropwise 27.5 ml (27.53 mmol) of a 1M solution of potassium tert-butoxide in tetrahydrofuran. The resulting mixture was stirred at room temperature for 18 hours. The solvent was evaporated off and the residue was partitioned between water and ethyl acetate. The organic phase was removed, washed with water and aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure, which gave 5.77 g (66% yield, 79% purity) of the product.

Workup

  1. customThe solvent was evaporated off
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic phase was removed
  4. washwashed with water and aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure, which
  8. customgave 5.77 g (66% yield, 79% purity) of the product

Sources & evidence

ORD record
ord-cd387ee420bd42c7949e98c970230938
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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