Sodium hydride → 2-(5-Bromo-4-chloro-alpha-cyano-2-methoxymethoxybenzyl)-3-methoxymethoxypyridine

HRID 862073Notes

Reaction equation

HRID 862073 reaction equation
[Br:1][C:2]1[C:3]([Cl:15])=[CH:4][C:5]([O:11][CH2:12][O:13][CH3:14])=[C:6]([CH:10]=1)[CH2:7][C:8]#[N:9].Br[C:17]1[C:22]([O:23][CH2:24][O:25][CH3:26])=[CH:21][CH:20]=[CH:19][N:18]=1.C1(C)C=CC(S([O-])=O)=CC=1.[Na+].[H-].[Na+]>C1COCC1>[Br:1][C:2]1[C:3]([Cl:15])=[CH:4][C:5]([O:11][CH2:12][O:13][CH3:14])=[C:6]([CH:10]=1)[CH:7]([C:17]1[C:22]([O:23][CH2:24][O:25][CH3:26])=[CH:21][CH:20]=[CH:19][N:18]=1)[C:8]#[N:9]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 2723791Sodium p-toluenesulfinateHCID 107559665-Bromo-4-chloro-2-methoxymethoxybenzyl cyanideHCID 115865732-Bromo-3-(methoxymethoxy)pyridine

Product 1

HCID 106701772-(5-Bromo-4-chloro-alpha-cyano-2-methoxymethoxybenzyl)-3-methoxymethoxypyridineYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-bromo-4-chloro-2-methoxymethoxybenzyl cyanide (10.4 g), 2-bromo-3-methoxymethoxy pyridine (7.81 g) and sodium p-toluenesulfinate (12.7 g) in THF (150 ml) was added, at room temperature, sodium hydride (3.63 g). The mixture was heated for 2 hours under reflux under argon atmosphere. The reaction mixture was cooled by aeration, which was poured into ice-water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution, dried (anhydrous magnesium sulfate) and concentrated. The crystal obtained was washed with cyclohexane/isopropyl ether (5:1) to give 2-(5-bromo-4-chloro-α-cyano-2-methoxymethoxybenzyl)-3-methoxymethoxypyridine (10.9 g) (Compound C-15). The physical properties and spectrum data are shown in Table 9 and Table 12.

Workup

  1. additionwas added, at room temperature
  2. temperatureThe mixture was heated for 2 hours
  3. temperatureunder reflux under argon atmosphere
  4. temperatureThe reaction mixture was cooled by aeration, which
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous saline solution
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. concentrationconcentrated
  9. customThe crystal obtained
  10. washwas washed with cyclohexane/isopropyl ether (5:1)

Sources & evidence

ORD record
ord-d32181553d664c0eb86fe1c05f5915ee
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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