Methanol → (5-Bromo-4-chloropyridin-2-yl)methanol

HRID 74596Notes

Reaction equation

HRID 74596 reaction equation
FC(F)(F)C(O[C:6](=[O:11])[C:7](F)(F)F)=O.[Br:14][C:15]1[C:16]([Cl:23])=[CH:17]C(C)=[N+:19]([O-])[CH:20]=1.CO>C(Cl)Cl>[Br:14][C:15]1[C:16]([Cl:23])=[CH:17][C:7]([CH2:6][OH:11])=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 9845Trifluoroacetic anhydrideHCID 136827785-Bromo-4-chloro-2-methylpyridine 1-oxide

Product 1

HCID 19791171(5-Bromo-4-chloropyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.0 mL trifluoroacetic anhydride were added dropwise at 10° C. to 2.6 g (12 mmol) 5-bromo-4-chloro-2-methylpyridine-1-oxide in 30 mL DCM. The reaction mixture was stirred for 5 days at RT. After the addition of MeOH the reaction mixture was evaporated down, the residue was combined with 15% potassium carbonate solution and extracted several times with EtOAC. The combined organic phases were dried on sodium sulphate and evaporated down.

Workup

  1. customwas evaporated down
  2. extractionextracted several times with EtOAC
  3. customThe combined organic phases were dried on sodium sulphate
  4. customevaporated down

Sources & evidence

ORD record
ord-3c280e930d3a4fb9aa6a1b2618d9a15a
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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