Hydrochloric Acid → 2-Fluoro-4-(hydroxymethyl)benzonitrile

HRID 1991233Notes

Reaction equation

HRID 1991233 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7](C=O)=[CH:6][C:3]=1[C:4]#[N:5].[BH4-].[Na+].Cl.[CH3:15][OH:16]>>[F:1][C:2]1[CH:9]=[C:8]([CH2:15][OH:16])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 27695822-Fluoro-5-formylbenzonitrileHCID 4311764Sodium borohydride

Product 1

HCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrile

Procedure

To a solution of 2-fluoro-5-formylbenzonitrile (350 mg, 2.4 mmol) in methanol (11 ml), at 0° C., was added sodium borohydride (107 mg, 2.8 mmol). The reaction mixture was allowed to warm to room temperature over 1 h, before addition of hydrochloric acid (1M, 30 ml). The mixture was extracted with ethyl acetate and the combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (354 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc4984d05fe84930a22e0462aecb2cfa
Source dataset
uspto-grants-2010_01
Patent number
US07645786B2

Reaction notes

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