Hydrogen Bromide → HCID 19689334, compound

HRID 975222Notes

Reaction equation

HRID 975222 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:16])[C:12]([F:15])([F:14])[F:13])=[CH:7][N:6]=1.Br.OO.O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)(Cl)Cl>[F:18][C:2]([F:1])([F:17])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 784Hydrogen PeroxideHCID 962WaterHCID 199715826-(2,2,2-Trifluoroethoxy)-α-(trifluoromethyl)-3-pyridinemethanol

Product 1

HCID 19689334HCID 19689334, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6212ChloroformSolvent

Procedure

2.6 g (0.0095 mol) of 2-(2,2,2-trifluoroethoxy)-5-(2,2,2-trifluoro-1-hydroxyethyl)pyridine and 0.18 g (0.0005 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 10 ml of chloroform at room temperature and 1.07 ml of a 48% strength aqueous solution of HBr are added. 4.24 ml (0.041 mol) of a 30% strength solution of H2O2 are slowly added dropwise at about 45° C. with vigorous stirring and the mixture is stirred for a further 24 hours. The reaction mixture is added to 200 ml of water, the phases are separated, the aqueous phase is extracted several times with chloroform and the combined organic phases are washed with 5% strength sodium bicarbonate solution and with water. After drying the organic phase with sodium sulfate, the volatiles are distilled off. Distillation of the crude product in a kugelrohr (25 torr, 100°-200° C. bath temperature) yields 1.65 g (60% of theory) of 2-(2,2,2-trifluoroethoxy)-5-trifluoroacetylpyridine, which, according to GC, is 98.3% pure.

Workup

  1. stirringthe mixture is stirred for a further 24 hours
  2. customthe phases are separated
  3. extractionthe aqueous phase is extracted several times with chloroform
  4. washthe combined organic phases are washed with 5% strength sodium bicarbonate solution and with water
  5. dry with materialAfter drying the organic phase with sodium sulfate
  6. distillationthe volatiles are distilled off
  7. distillationDistillation of the crude product in a kugelrohr (25 torr, 100°-200° C. bath temperature)

Sources & evidence

ORD record
ord-45f3c3a0c4cf44519e1769b92f050126
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

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