Methyl iodide → 4-Bromo-1-methanesulfonyl-2-(trifluoromethoxy)benzene

HRID 2103639Notes

Reaction equation

HRID 2103639 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](S)=[C:4]([O:9][C:10]([F:13])([F:12])[F:11])[CH:3]=1.IC.[C:16](=O)([O-])[O-].[K+].[K+].BrC1C=CC(SC)=C(OC(F)(F)F)C=1.O[O:37][S:38]([O-:40])=O.[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:38]([CH3:16])(=[O:40])=[O:37])=[C:4]([O:9][C:10]([F:13])([F:12])[F:11])[CH:3]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27364254-Bromo-2-(trifluoromethoxy)thiophenolHCID 187114734-Bromo-2-(trifluoromethoxy)thioanisoleHCID 23707502Potassium hydroxy sulfite3×

Product 1

HCID 534180354-Bromo-1-methanesulfonyl-2-(trifluoromethoxy)benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the method of example 9a, reaction of 4-bromo-2-trifluoromethoxy-benzenethiol (1.0 g, 3.48 mmol) with iodomethane (0.238 mL, 3.82 mmol) and potassium carbonate (0.528 g, 3.82 mmol) in 13 mL acetone, followed by oxidation as described in example 39c, using 4-bromo-1-methylsulfanyl-2-trifluoromethoxy-benzene (0.78 g, 2.72 mmol) and oxone® (2.17 g, 3.54 mmol), stirring over night at r.t., addition of oxone® (0.84 g, 1.37 mmol), stirring over night at r.t., addition of oxone® (0.84 g, 1.37 mmol) and stirring over three days at r.t. affords the title compound without further chromatography as a white solid (0.81 g). MS (m/e): 320 (M+H).

Workup

  1. stirringstirring over night at r.t.
  2. stirringstirring over three days at r.t.

Sources & evidence

ORD record
ord-5b68ea12096e497bbccaaf09405d7928
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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