Trifluoroacetic anhydride → 3-Bromo-2-chloro-6-methylpyridin-1-ium-1-olate

HRID 2196409

Reaction equation

HRID 2196409 reaction equation
[Br:1][C:2]1[C:3]([Cl:9])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.OO.NC(N)=[O:14].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:9])=[N+:4]([O-:14])[C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 27344183-Bromo-2-chloro-6-methylpyridine

Product 1

HCID 857064893-Bromo-2-chloro-6-methylpyridin-1-ium-1-olateYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-bromo-2-chloro-6-methylpyridine (1 g, 4.84 mmol) and urea hydrogen peroxide (911 mg, 9.69 mmol) in DCM (24 mL) at 0° C. was added trifluoroacetic anhydride (1.4 mL, 9.69 mmol). After warming to 25° C. over 12 h, the solution was partitioned between H2O-DCM. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (silica, 1% MeOH in DCM) yielding the title compound (1.1 g, quant.) as a white solid: LCMS (ES) m/z=223 (M+H)+.

Workup

  1. customthe solution was partitioned between H2O-DCM
  2. washThe aqueous phase was washed several times with DCM
  3. dry with materialthe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified via column chromatography (silica, 1% MeOH in DCM)

Sources & evidence

ORD record
ord-f0377ca4ecf94504b22964cc4b9605f3
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Linked notes

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