Methyl iodide → HCID 18782518, compound

HRID 1420814Notes

Reaction equation

HRID 1420814 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:4][C:3]=1[OH:14].[C:15]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([F:12])([F:13])[F:11])[CH:5]=[CH:4][C:3]=1[O:14][CH3:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18782560Phenol, 2-bromo-4-(2,2,2-trifluoroethoxy)-

Product 1

HCID 18782518HCID 18782518, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-bromo-4-(2,2,2-trifluoroethoxy)phenol (Description 20, 0.6 g) in acetone was added added K2CO3 (1 g) and methyl iodide (1 ml). The solution was heated to reflux for 1 h. and then evaporated in vacuo. The residue was partitioned between ethyl acetate and water and the organic phase washed further with water and saturated brine. After drying (MgSO4) the solvent was removed in vacuo to give the title compound as a yellow oil. 1H NMR (250 MHz, CDCl3) δ3.87 (3H, s) 4.30 (2H, q, J 8 Hz), 6.82-6.92 (2H, m), and 7.20 (1H, d, J 3 Hz).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 h.
  3. customevaporated in vacuo
  4. customThe residue was partitioned between ethyl acetate and water
  5. washthe organic phase washed further with water and saturated brine
  6. dry with materialAfter drying (MgSO4) the solvent
  7. customwas removed in vacuo

Sources & evidence

ORD record
ord-cf82aac6c4754cae93eaf342eebef1a8
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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