Sodium Chloride → 4-Formyl-3-methylbenzonitrile

HRID 343922Notes

Reaction equation

HRID 343922 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].C([Li])CCC.CN(C)[CH:18]=[O:19].[Cl-].[Na+]>O1CCCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([CH:18]=[O:19])=[C:3]([CH3:10])[CH:4]=1)#[N:7]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 27374944-Bromo-3-methylbenzonitrileHCID 178418339Butyllithium

Product 1

HCID 109096954-Formyl-3-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-100 °C

Procedure

To a stirred solution of 4-bromo-3-methylbenzonitrile (4 g, 20 mmol) in tetrahydrofuran (100 ml), cooled to -100° C. under a nitrogen atmosphere, was added dropwise a solution of n-butyllithium in hexanes (1.6M, 12.8 ml). After addition, the pale red solution was stirred for 5 minutes at -100° C. and dry dimethylformamide (2.2 ml) then added dropwise. After 20 minutes, during which the temperature reached -60° C., the reaction mixture was poured onto a saturated solution of sodium chloride (100 ml). The organic phase was separated and combined with a diethyl ether (100 ml) wash of the aqueous phase, dried, filtered and evaporated. Crystallised from diethyl ether-hexane to give 4-cyano-2-methylbenzaldehyde as a white solid.

Workup

  1. additionAfter addition
  2. waitAfter 20 minutes
  3. customreached -60° C.
  4. customThe organic phase was separated
  5. washwash of the aqueous phase
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customCrystallised from diethyl ether-hexane

Sources & evidence

ORD record
ord-601a89a848504c77b491d684b75818a0
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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