Methyl iodide → 3,5-Bis(trifluoromethyl)anisole

HRID 2167360Notes

Reaction equation

HRID 2167360 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CI.[C:18]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:18][O:13][C:5]1[CH:4]=[C:3]([C:2]([F:14])([F:15])[F:1])[CH:8]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 676803,5-Bis(trifluoromethyl)phenol

Product 1

HCID 27378043,5-Bis(trifluoromethyl)anisoleYield 56.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3,5-bis(trifluoromethyl)phenol (47, 1.0 g, 4.35 mmol), methyl iodide (0.7 mL, 10.8 mmol) and K2CO3 (3 g, 21.75 mmol) in acetone (10 mL) was heated to reflux while stirring overnight. Solid residue was filtered off and the filtrate was concentrated on warm water bath at atmospheric pressure (Caution: product was volatile) to afford 1-methoxy-3,5-bis(trifluoromethyl)benzene (48, 0.6 g, 56%) as clear oil: 1H NMR (300 MHz, CDCl3) δ 7.46 (s, 1H), 7.30 (s, 1H), 3.90 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationSolid residue was filtered off
  4. concentrationthe filtrate was concentrated
  5. temperatureon warm water bath at atmospheric pressure (Caution: product was volatile)

Sources & evidence

ORD record
ord-f043137f3bf645a1bf4ec5eb9de7efc0
Source dataset
uspto-grants-2015_06
Patent number
US09045445B2

Reaction notes

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