Sodium Methoxide → HCID 19068732, compound

HRID 1957258Notes

Reaction equation

HRID 1957258 reaction equation
[CH3:1][O-:2].[Na+].Br[CH2:5][C:6]1[CH:7]=[C:8]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=2)[CH:9]=[CH:10][C:11]=1[Cl:12]>CO>[Cl:19][C:18]1[C:13]([C:8]2[CH:9]=[CH:10][C:11]([Cl:12])=[C:6]([CH2:5][O:2][CH3:1])[CH:7]=2)=[N:14][CH:15]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:17]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18692940HCID 18692940, compound

Product 1

HCID 19068732HCID 19068732, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

7.0 g of a 30% by weight solution of sodium methoxide in methanol were added to a solution of 5.0 g of 2-(3-bromomethyl-4-chlorophenyl)-3-chloro-5-trifluoromethylpyridine in 100 ml of anhydrous methanol. The mixture was refluxed for 8 hours and then concentrated. The residue was taken up in 100 ml of 10% strength hydrochloric acid, after which three extractions with 50 ml of ether each time were carried out. The ether phases were dried over sodium sulfate and concentrated. The oily residue was induced to crystallize with a little cold cyclohexane. Yield: 2.9 g (67%) of colorless crystals; melting point: 52°-54° C.

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. concentrationconcentrated
  3. extractionafter which three extractions with 50 ml of ether each time
  4. dry with materialThe ether phases were dried over sodium sulfate
  5. concentrationconcentrated
  6. customto crystallize with a little cold cyclohexane

Sources & evidence

ORD record
ord-391e4b70a0d34d0c8e305e1c77bf5c13
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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