Diisobutylaluminum hydride → 2-Fluoro-5-(1-oxopropan-2-yl)benzonitrile

HRID 2173231Notes

Reaction equation

HRID 2173231 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]([CH3:15])[C:11](OC)=[O:12])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].CC(C[AlH]CC(C)C)C>C1COCC1>[F:9][C:8]1[CH:7]=[CH:6][C:5]([CH:10]([CH3:15])[CH:11]=[O:12])=[CH:4][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 67517528Methyl 2-(3-cyano-4-fluorophenyl)propanoate

Product 1

HCID 874292652-Fluoro-5-(1-oxopropan-2-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound methyl 2-(3-cyano-4-fluorophenyl)propanoate (50 mg, 0.24 mmol) in 5 mL of anhydrous THF was cooled to 0° C. and then added DIBAL-H (0.3 mmol) was added. The mixture was warmed to ambient temperature and stirred at ambient temperature for 1.5 hours. The reaction was quenched with water, extracte with EtOAc. The organic layer was washed with saturated chloride, dried over anhydrous sodium sulfate and concentrated. The 2-fluoro-5-(1-oxopropan-2-yl)benzonitrile was used for next step without purification.

Workup

  1. customThe reaction was quenched with water, extracte with EtOAc
  2. washThe organic layer was washed with saturated chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe 2-fluoro-5-(1-oxopropan-2-yl)benzonitrile was used for next step without purification

Sources & evidence

ORD record
ord-88859a80a4bb42f8941660852d579e1d
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…