2-Fluoro-5-formylbenzonitrile → 2-Fluoro-5-(1-hydroxyethyl)benzonitrile

HRID 1501973Notes

Reaction equation

HRID 1501973 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH:6]=[O:7])#[N:2].[CH3:12][Mg]Br>C1COCC1>[F:11][C:10]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH3:12])=[CH:4][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 27695822-Fluoro-5-formylbenzonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 577800282-Fluoro-5-(1-hydroxyethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

3-Cyano-4-fluorobenzaldehyde (2.17 g, 14.7 mmol) was dissolved in THF (50 mL) then cooled to −70° C. To this mixture was added methyl magnesium bromide (5.34 mL, 16.0 mmol). The mixture was stirred for 1 h, then was quenched with brine and extracted with ether. The ethereal layer was separated, dried over Na2SO4, filtered, and evaporated to dryness. The residue was purified by MPLC chromatography through a 120 g Redi-sep column using 0-50% EtOAc/hexane eluent to yield 2-fluoro-5-(1-hydroxyethyl)benzonitrile: LC-MS: M+1=166.

Workup

  1. customwas quenched with brine
  2. extractionextracted with ether
  3. customThe ethereal layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by MPLC chromatography through a 120 g Redi-sep column

Sources & evidence

ORD record
ord-83dc94fad154466ebd47a06e3c45911d
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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