Acetic Acid → HCID 178426049, compound

HRID 2106799Notes

Reaction equation

HRID 2106799 reaction equation
Br.C[O:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][N:5]=1.C(O)(=O)C>O>[CH3:10][C:9]1[C:4]([OH:3])=[N:5][CH:6]=[C:7]([C:11]([F:14])([F:12])[F:13])[CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 111168552-Methoxy-3-methyl-5-(trifluoromethyl)pyridine

Product 1

HCID 178426049HCID 178426049, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Two ml of 48 percent hydrobromic acid were added with stirring to mixture of 1.38 g (5.5 mol) of 2-methoxy-3-methyl-5-(trifluoromethyl)pyridine and 6 ml of glacial acetic acid at 100° C. and the mixture was allowed to react at about 95° C. for 20 min. The mixture was then cooled and poured onto ice and the solid that formed was collected by filtration. A second crop of solid was obtained by adding more water to the filtrate. The combined solids were dried to obtain 0.40 g (40 percent of theory) of the title compound as a white powder melting at 141°-143° C. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. customto react at about 95° C. for 20 min
  2. temperatureThe mixture was then cooled
  3. additionpoured onto ice
  4. customthe solid that formed
  5. filtrationwas collected by filtration
  6. customA second crop of solid was obtained
  7. customThe combined solids were dried

Sources & evidence

ORD record
ord-ff2ef003c4d04db19975118f21bb61c2
Source dataset
uspto-grants-1990_06
Patent number
US04931452

Reaction notes

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