Ammonium Chloride → (3,5-Difluoro-4-((6-(trifluoromethyl)-3-pyridinyl)oxy)phenyl)methanol

HRID 920286Notes

Reaction equation

HRID 920286 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:21])[C:9]=1[O:10][C:11]1[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=1)[CH:5]=[O:6].[BH4-].[Na+].[NH4+].[Cl-]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([F:21])[C:9]=1[O:10][C:11]1[CH:12]=[N:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 866763653,5-Difluoro-4-((6-(trifluoromethyl)-3-pyridinyl)oxy)benzaldehyde

Product 1

HCID 66825487(3,5-Difluoro-4-((6-(trifluoromethyl)-3-pyridinyl)oxy)phenyl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5-difluoro-4-((6-(trifluoromethyl)pyridin-3-yl)oxy)benzaldehyde (1.78 g, 5.87 mmol) in methanol (15 mL) was added NaBH4 (0.222 g, 5.87 mmol). The mixture was stirred at room temp for 0.5 h. NH4Cl solution was added to the reaction mixture, and the reaction mixture was extracted by DCM. The organic phase was then dried over Na2SO4 and evaporated to give the product (1.702 g, 95%).

Workup

  1. extractionthe reaction mixture was extracted by DCM
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-ab5404f3f6314f2cba81ed55e941432d
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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