Sodium borohydride → 2-Fluoro-4-(3-hydroxy-1-propyl)benzonitrile

HRID 412193Notes

Reaction equation

HRID 412193 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](OCC)=[O:12])=[CH:5][C:4]=1[F:16])#[N:2].[BH4-].[Na+]>C(O)C>[F:16][C:4]1[CH:5]=[C:6]([CH2:9][CH2:10][CH2:11][OH:12])[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 18536111HCID 18536111, compound

Product 1

HCID 185360712-Fluoro-4-(3-hydroxy-1-propyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the product from Step C (140 mg, 0.71 mmol) in 3.5 mL of ethanol at 0° C. was added sodium borohydride (84 mg, 2.1 mmol). After 45 minutes, another portion of sodium borohydride was added, and the mixture was stirred overnight. The reaction was quenched with saturated NH4Cl solution, concentrated in vacuo, and partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the alcohol which was sufficiently pure for use in the next step without further purification.

Workup

  1. customThe reaction was quenched with saturated NH4Cl solution
  2. concentrationconcentrated in vacuo
  3. custompartitioned between EtOAc and saturated NaHCO3 solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ac9113e3c274ce586405de51822ba11
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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