Sodium potassium tartrate tetrahydrate → HCID 71606902, compound

HRID 623946Notes

Reaction equation

HRID 623946 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:12]C)[C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(O)(=O)C.Br.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5]([C:8]([F:9])([F:10])[F:11])=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 2724148Sodium potassium tartrate tetrahydrateHCID 576341775-Bromo-3-methoxy-2-(trifluoromethyl)pyridine

Product 1

HCID 71606902HCID 71606902, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 5-bromo-3-methoxy-2-(trifluoromethyl)pyridine (28) (0.87 g, 3.4 mmol) in a mixture of acetic acid (6 mL) and 33% HBr in acetic acid (12 mL) was stirred at 110° C. in a sealed tube overnight. Then Potassium Sodium tartrate tetrahydrate (7.8 g) was added slowly under 0° C. The mixture was taken up in ethyl acetate after 10 minutes stirring, the organic phase was washed with brine, dried over Na2SO4. The extract was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a gradient of Hexane-Ethyl acetate (1:2) as the eluent to give the product (29) 0.65 g as gray solid, Yield: 79%. 1H NMR (CD3OD, 400 MHz): δ 8.18 (s, 1H), 7.58 (s, 1H). 19F NMR (CDCl3, 376 MHz): −68.0.

Workup

  1. stirringstirring
  2. washthe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe extract was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using a gradient of Hexane-Ethyl acetate (1:2) as the eluent

Sources & evidence

ORD record
ord-356d1c9596b64bff829f5f2057c3747f
Source dataset
uspto-grants-2016_04
Patent number
US09303017B2

Reaction notes

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