Methyl iodide → 5-Bromo-1,2-difluoro-3-methoxybenzene

HRID 1522874Notes

Reaction equation

HRID 1522874 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.[C:11]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:11])[C:5]([F:9])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27733075-Bromo-2,3-Difluorophenol

Product 1

HCID 27732885-Bromo-1,2-difluoro-3-methoxybenzeneYield 94.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-bromo-2,3-difluorophenol (19 g, 90 mmol) in acetone (180 mL), K2CO3 (18 g, 0.13 mol) and iodomethane (25.8 g, 0.18 mol) were added. The resulting mixture was refluxed for 4 h. Upon completion, the mixture was cooled to room temperature and filtered, and the filtrate was evaporated to give the crude product, which was further purified by column chromatography on silica gel (eluting with petroleum ether/ethyl acetate=80/1-40/1) to give a light yellow liquid 5-bromo-1,2-difluoro-3-methoxybenzene (19 g). 1H NMR (CDCl3): δ 7.00-6.88 (m, 2H), 3.89 (s, 3H).

Workup

  1. temperatureThe resulting mixture was refluxed for 4 h
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. customto give the crude product, which
  5. customwas further purified by column chromatography on silica gel (eluting with petroleum ether/ethyl acetate=80/1-40/1)

Sources & evidence

ORD record
ord-af3253632770410c9e6df9b103c9172f
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

Loading…