Sodium borohydride → HCID 59370515, compound

HRID 2046651Notes

Reaction equation

HRID 2046651 reaction equation
[F:1][C:2]1[C:9]([CH:10]=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.FC1C=CC(C#N)=C(C(F)(F)F)C=1C=O.[BH4-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[F:1][C:2]1[C:9]([CH2:10][OH:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:12]([F:13])([F:14])[F:15])[CH:3]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 713331064-Fluoro-3-formyl-2-(trifluoromethyl)benzonitrileHCID 862572524-Fluoro-5-formyl-2-(trifluoromethyl)benzonitrile

Product 1

HCID 59370515HCID 59370515, compoundYield 44.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution (15 mL) of a mixture (1.01 g) of 4-fluoro-5-formyl-2-(trifluoromethyl)benzonitrile and 4-fluoro-3-formyl-2-(trifluoromethyl)benzonitrile (3:1) in tetrahydrofuran was added sodium borohydride (400 mg) at 0° C., and the mixture was stirred at room temperature for 12 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=5:1→1:4) to give the title compound as a yellow oil (yield: 456 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=5:1→1:4)

Sources & evidence

ORD record
ord-e29e1666441f44a3bd3e3e7fb7beeb73
Source dataset
uspto-grants-2013_11
Patent number
US08592452B2

Reaction notes

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