Sodium hydride → 2-(5-Bromo-alpha-cyano-2-methoxymethoxybenzyl)-3-trifluoromethyl-pyridine

HRID 862079Notes

Reaction equation

HRID 862079 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:14][O:15][CH3:16])=[C:8]([CH:12]=1)[CH2:9][C:10]#[N:11].Cl[C:18]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][N:19]=1.C1(C)C=CC(S([O-])=O)=CC=1.[Na+]>CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:14][O:15][CH3:16])=[C:8]([CH:12]=1)[CH:9]([C:18]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][N:19]=1)[C:10]#[N:11]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 2723791Sodium p-toluenesulfinateHCID 197016225-Bromo-2-methoxymethoxybenzyl cyanide

Product 1

HCID 197016212-(5-Bromo-alpha-cyano-2-methoxymethoxybenzyl)-3-trifluoromethyl-pyridineYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sixty % sodium hydride (656 mg) was added, at room temperature, to a mixture of 5-bromo-2-methoxymethoxybenzyl cyanide (3.50 g), 2-chloro-3-trifluoromethylpyridine (2.48 g), sodium p-toluenesulfinate (731 mg) and DMF (35 ml), followed by stirring for 30 minutes at the same temperature under argon atmosphere. The reaction mixture was poured into an aqueous saline solution, followed by extraction with ethyl acetate. The extract solution was washed with an aqueous saline solution, dried (anhydrous sodium sulfate) and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane) to give 2-(5-bromo-α-cyano-2-methoxymethoxybenzyl)-3-trifluoromethyl-pyridine (2.63 g) (Compound D-4). The physical properties and spectrum date are shown in Table 13 and Table 14.

Workup

  1. additionThe reaction mixture was poured into an aqueous saline solution
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract solution was washed with an aqueous saline solution
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-866fbdae74064f1b922de30c2f7a7604
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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