Sodium Chloride → 4-Formyl-2-methoxybenzonitrile

HRID 1519572Notes

Reaction equation

HRID 1519572 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[Li]CCCC.CN([CH:20]=[O:21])C.[Cl-].[Na+]>C1COCC1>[CH:20]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1)=[O:21]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 223467024-Bromo-2-methoxybenzonitrileHCID 178418339Butyllithium

Product 1

HCID 600485344-Formyl-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 4-bromo-2-methoxybenzonitrile (1.0 g, 4.7 mmol) in 30 mL of anhydrous THF was added BuLi (1.6 M, 3.3 mL, 5.2 mmol) 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 (0.6 mL) then added dropwise. After 20 min, the reaction mixture was poured onto a saturated solution of sodium chloride (50 mL). The organic phase was separated, extracted with diethyl ether (100 mL), dried over Na2SO4 and distilled off the solvent to afford 4-formyl-2-methoxybenzonitrile. MS m/z: 162 (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-22b981d1dc0c40fbbf250bf7140ea72e
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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