Methyl iodide → 3-Fluoro-4-nitroanisole

HRID 1725335Notes

Reaction equation

HRID 1725335 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[C:12]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 5656543-Fluoro-4-nitroanisoleYield 69%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

28 g (0.2 mole) of 3-fluoro-4-nitrophenol was dissolved in 200 mL of acetone. 56 g (0.4 mole) of K2CO3 was added, and the contents heated to 40 C for 10 min. Contents were cooled to 0 C, 25 mL (0.4 mole) of methyl iodide added, and again heated to 40 C for 3 hrs. Reaction cooled to rt, roto-evaporated to approx. 100 mL, and 200 mL of methylene chloride was added. Contents were filtered, and the filtrant was rotary-evaporated to dryness. The crystalline solid was recrystallized from 4:1 EtOH/H2O to give 23.6 g (46%) of desired product. 1H NMR (CDCl3, 400 MHz) 8.12 (m, 1H), 6.78 (m, 2H), 3.93 (s, 3H); LCMS (M+H)+ 172 found.

Workup

  1. temperaturethe contents heated to 40 C for 10 min
  2. additionadded
  3. temperatureagain heated to 40 C for 3 hrs
  4. customReaction
  5. customroto-evaporated to approx. 100 mL, and 200 mL of methylene chloride
  6. additionwas added
  7. filtrationContents were filtered
  8. customthe filtrant was rotary-evaporated to dryness
  9. customThe crystalline solid was recrystallized from 4:1 EtOH/H2O

Sources & evidence

ORD record
ord-8a8cc5687f464b2b96dd2710dbee6b1f
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

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