Trifluoroacetic anhydride → (3-Bromo-5-fluoro-4-methyl-2-pyridyl)methanol

HRID 1502465Notes

Reaction equation

HRID 1502465 reaction equation
FC(F)(F)C(O[C:6](=[O:11])[C:7](F)(F)F)=O.[Br:14][C:15]1C(C)=[N+:17]([O-])[CH:18]=[C:19]([F:22])[C:20]=1[CH3:21]>C(Cl)Cl.C(OCC)(=O)C>[Br:14][C:15]1[C:7]([CH2:6][OH:11])=[N:17][CH:18]=[C:19]([F:22])[C:20]=1[CH3:21]

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 679750773-Bromo-5-fluoro-2,4-dimethylpyridine 1-oxide

Product 1

HCID 67974745(3-Bromo-5-fluoro-4-methyl-2-pyridyl)methanolYield 68.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic anhydride (0.35 mL, 2.5 mmol) was added dropwise to a solution of 3-bromo-5-fluoro-2,4-dimethylpyridine 1-oxide (220 mg; 1.0 mmol) in DCM (3 mL). The reaction mixture was stirred at room temperature overnight and then diluted with ethyl acetate (50 mL) and washed with saturated aqueous sodium bicarbonate solution (20 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue that was purified by flash chromatography (4 g, Silica, 0-100% ethyl acetate in heptane). Desired fractions were combined and evaporated in vacuo to afford the title compound as a pale yellow oil (150 mg, 68%), which was used in the next step without further purification.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution (20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a residue that
  7. customwas purified by flash chromatography (4 g, Silica, 0-100% ethyl acetate in heptane)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-c5c2923ce85d43bca875a89d41b3e143
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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