Dimethylformamide → 2-(5-Bromo-4-chloro-2-methoxymethoxybenzoyl)-3-methoxymethoxypyridine

HRID 862074Notes

Reaction equation

HRID 862074 reaction equation
CN(C=[O:5])C.[Br:6][C:7]1[C:8]([Cl:30])=[CH:9][C:10]([O:26][CH2:27][O:28][CH3:29])=[C:11]([CH:25]=1)[CH:12]([C:15]1[C:20]([O:21][CH2:22][O:23][CH3:24])=[CH:19][CH:18]=[CH:17][N:16]=1)C#N.C(=O)([O-])[O-].[K+].[K+]>O>[Br:6][C:7]1[C:8]([Cl:30])=[CH:9][C:10]([O:26][CH2:27][O:28][CH3:29])=[C:11]([CH:25]=1)[C:12]([C:15]1[C:20]([O:21][CH2:22][O:23][CH3:24])=[CH:19][CH:18]=[CH:17][N:16]=1)=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 106701772-(5-Bromo-4-chloro-alpha-cyano-2-methoxymethoxybenzyl)-3-methoxymethoxypyridine

Product 1

HCID 108357432-(5-Bromo-4-chloro-2-methoxymethoxybenzoyl)-3-methoxymethoxypyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DMF (100 ml) was added to a mixture of 2-(5-bromo-4-chloro-α-cyano-2-methoxymethoxybenzyl)-3-methoxymethoxypyridine (10.1 g) and potassium carbonate (9.84 g). The mixture was stirred at room temperature overnight under oxygen atmosphere. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution, dried (anhydrous magnesium sulfate), and concentrated. The concentrate was purified by a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 2-(5-bromo-4-chloro-2-methoxymethoxybenzoyl)-3-methoxymethoxypyridine (9.08 g, m.p. 70°-72° C.). The spectrum data are shown as follows:

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous saline solution
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. concentrationconcentrated
  5. customThe concentrate was purified by a silica gel column chromatography (eluted with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6bf6bd41ec3b4f6d8dc0724dfd18e59b
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

Loading…