Sodium Chloride → 4-Formyl-3-methylbenzonitrile

HRID 1519576Notes

Reaction equation

HRID 1519576 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[Li]CCCC.CN([CH:19]=[O:20])C.[Cl-].[Na+]>C1COCC1>[CH:19]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10])=[O:20]

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
-78 °C

Procedure

To a stirred solution of 4-bromo-3-methylbenzonitrile (4.0 g, 20 mmol) in 100 mL of anhydrous THF was added BuLi (1.6 M, 12.8 mL) dropwise at −78° C. under nitrogen atmosphere. After the addition, the pale red solution was stirred for 5 min at −78° C. and dry DMF (2.2 mL) then added drop wise. After 20 min, the reaction mixture was poured onto a saturated solution of sodium chloride (100 mL). The organic phase was separated, extracted with diethyl ether (100 mL), dried over Na2SO4 and distilled off the solvent to afford 3.5 g of crude 4-formyl-3-methylbenzonitrile. MS m/z: 146 (M+1)+.

Workup

  1. additionAfter the addition
  2. waitAfter 20 min
  3. customThe organic phase was separated
  4. extractionextracted with diethyl ether (100 mL)
  5. dry with materialdried over Na2SO4
  6. distillationdistilled off the solvent

Sources & evidence

ORD record
ord-93c89b17f07b4ee9b99c2099a3e1be86
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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