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Sodium borohydride → 3-(4-(3-(Trifluoromethyl)phenoxy)phenyl)propanenitrile

HRID 705844
Notes
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Reaction equation

HRID 705844 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]#[N:16])=[CH:9][CH:8]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]([F:20])([F:21])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][C:15]#[N:16])=[CH:11][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 677761303-(4-(3-(Trifluoromethyl)phenoxy)phenyl)acrylonitrile

Product 1

HCID 677751713-(4-(3-(Trifluoromethyl)phenoxy)phenyl)propanenitrileYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-(4-(3-(trifluoromethyl)phenoxy)phenyl)acrylonitrile (5 g, 17.29 mmol) in Ethanol (80 mL) was added NaBH4 (4.5 g, 119 mmol). The reaction mixture was stirred at 70° C. overnight. After cooling to room temperature, the reaction mixture was quenched with water (50 mL), and ethanol was removed under reduced pressure. The residue was partitioned between EA (100 mL) and water (50 mL). The organic phase was washed with saturated NaHCO3 solution (80 mL), brine (50 mL), dried over sodium sulfate, concentrated, and purified via flash chromatography to afford the title compound (4.3 g, 13.89 mmol, 80% yield) as colorless oil. LCMS: rt=1.64 min, no MS signal

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was quenched with water (50 mL), and ethanol
  3. customwas removed under reduced pressure
  4. customThe residue was partitioned between EA (100 mL) and water (50 mL)
  5. washThe organic phase was washed with saturated NaHCO3 solution (80 mL), brine (50 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. custompurified via flash chromatography

Sources & evidence

ORD record
ord-079c2862470441a8a178923bbb4fea6e
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09174968B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes