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

HRID 2175799Notes

Reaction equation

HRID 2175799 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 magnesiumbromide (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-c9793e99ff3741908fcf7439538d093c
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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