5-Cyano-2-fluorobenzaldehyde → 4-Fluoro-3-(1-hydroxyethyl)benzonitrile

HRID 398357Notes

Reaction equation

HRID 398357 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:11])=[C:7]([CH:10]=1)[CH:8]=[O:9])#[N:2].[CH3:12][Li]>C1COCC1>[F:11][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:10][C:7]=1[CH:8]([OH:9])[CH3:12]

Participants

4

Reactant 2

HCID 109097255-Cyano-2-fluorobenzaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 230001664-Fluoro-3-(1-hydroxyethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-cyano-2-fluorobenzaldehyde (1.50 g, 10.06 mmol) in THF (15 mL) cooled to 0° C. was added methyllithium (7.90 mL, 11.06 mmol). The mixture was stirred at room temperature for 2 h and quenched by the addition of saturated NH4Cl (10 mL). The mixture was partitioned between ethyl acetate (50 mL) and water (20 mL), the organic was washed with water (20 mL), dried over magnesium sulfate and concentrated in vacuo to provide a residue. Purification via flash column chromatography (30×150 mm column; elution with EtOAc: Hex, 1:2) afforded pure compound:

Workup

  1. customquenched by the addition of saturated NH4Cl (10 mL)
  2. customThe mixture was partitioned between ethyl acetate (50 mL) and water (20 mL)
  3. washthe organic was washed with water (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto provide a residue
  7. customPurification
  8. washvia flash column chromatography (30×150 mm column; elution with EtOAc: Hex, 1:2)
  9. customafforded pure compound

Sources & evidence

ORD record
ord-78c9206df81240b7876af20d7576b8a9
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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