Bromine → 4-Bromo-5-methoxy-2-(trifluoromethyl)pyridine

HRID 1976070Notes

Reaction equation

HRID 1976070 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[N:7][C:8]([C:15]([F:18])([F:17])[F:16])=[CH:9][C:10]=1[Sn](C)(C)C.[O-]S([O-])=O.[Na+].[Na+]>ClCCl>[Br:1][C:10]1[CH:9]=[C:8]([C:15]([F:18])([F:17])[F:16])[N:7]=[CH:6][C:5]=1[O:4][CH3:3]

Participants

5

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 22000206HCID 22000206, compound

Product 1

HCID 220001724-Bromo-5-methoxy-2-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (0.52 ml, 10 mmol) was added via syringe to a stirred solution of 3-methoxy-6-trifluoromethyl-4-trimethylstannylpyridine (1.7 g, 5 mmol) in dichloromethane (25 ml). The reaction mixture was stirred for 30 min at room temperature and treated with saturated aqueous Na2SO3 (15 ml). The phases were separated. The aqueous layer was extracted with dichloromethane (2×15 ml). The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (hexane:ethyl acetate 0-15%) to afford 4-bromo-3-methoxy-6-trifluoromethylpyridine as a white solid.

Workup

  1. customThe phases were separated
  2. extractionThe aqueous layer was extracted with dichloromethane (2×15 ml)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (hexane:ethyl acetate 0-15%)

Sources & evidence

ORD record
ord-76f1a9e0d81749c380c2edc295b15b35
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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