Dimethylformamide → 4-Formyl-3-methylbenzonitrile

HRID 2410135Notes

Reaction equation

HRID 2410135 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].CN([CH:14]=[O:15])C>C1COCC1>[CH:14]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10])=[O:15]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 27374944-Bromo-3-methylbenzonitrile

Product 1

HCID 109096954-Formyl-3-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of 4-bromo-3-methylbenzonitrile (20 g, 102 mmol) in THF (500 mL) at −100° C. was slowly added a solution of n-Buli 1.6M in hexanes (70 mL, 112 mmol). DMF (11 mL, 143 mmol) was then added and the mixture was allowed to warm to −50° C. over 30 min. The reaction mixture was quenched with brine. The reaction mixture was diluted with EtOAc and extracted with brine. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (hexane/EtOAc, 80:20) the residue was triturated in Et2O/hexane 90:10 to afford the title compound. tR: 0.86 min (LC-MS 2); Rf=0.40 (hexane/EtOAc, 8:2).

Workup

  1. customThe reaction mixture was quenched with brine
  2. additionThe reaction mixture was diluted with EtOAc
  3. extractionextracted with brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (hexane/EtOAc, 80:20) the residue
  8. customwas triturated in Et2O/hexane 90:10

Sources & evidence

ORD record
ord-5d3c929c9cb148a3ae1b451136c8337c
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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