Water → 2-(3-Bromo-4-cyanobenzoyl)-3-methoxymethoxypyridine

HRID 442723Notes

Reaction equation

HRID 442723 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1F)[C:5]([C:7]1[C:12]([O:13][CH2:14][O:15][CH3:16])=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6].[C-:21]#[N:22].[K+].O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[C:21]#[N:22])[C:5]([C:7]1[C:12]([O:13][CH2:14][O:15][CH3:16])=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 539864842-(3-Bromo-4-fluorobenzoyl)-3-methoxymethoxypyridine

Product 1

HCID 544552472-(3-Bromo-4-cyanobenzoyl)-3-methoxymethoxypyridineYield 96.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-(3-bromo-4-fluorobenzoyl)-3-methoxymethoxypyridine (4.68 g) in dimethyl sulfoxide (50 mL) was added potassium cyanide (2.7 g) at 0° C. The mixture was stirred for 3 hours while raising the temperature to room temperature. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The extract solution was washed with water and a saturated aqueous saline solution, successively, and dried (sodium sulfate) and then concentrated. The concentrate was purified by means of a silica gel column (ethyl acetate--hexane) to afford 2-(3-bromo-4-cyanobenzoyl)-3-methoxymethoxypyridine (4.59 g) (compound B-6). Physical properties and spectrum date of the product are shown in Table 3 and Table 4.

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe extract solution was washed with water
  3. dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe concentrate was purified by means of a silica gel column (ethyl acetate--hexane)

Sources & evidence

ORD record
ord-cab4986e594f492b889eb9289780a412
Source dataset
uspto-grants-1999_04
Patent number
US05891895

Reaction notes

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