Methyl iodide → 2-Fluoro-6-nitroanisole

HRID 2175875Notes

Reaction equation

HRID 2175875 reaction equation
CI.[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[OH:13].[C:14]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[O:13][CH3:14]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 737102-Fluoro-6-nitrophenol

Product 1

HCID 5986062-Fluoro-6-nitroanisole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

MeI (27.1 g, 191 mmol) was added dropwise to the suspension of 2-fluoro-6-nitrophenol (25.0 g, 159 mmol) and K2CO3 (44.0 g, 318 mmol) in 200 mL of DMF. The mixture was stirred overnight at 25° C. then warmed to 60° C. and stirred for 3 hours. The mixture was diluted with 1 L of EtOAc and washed with water (3×100 mL) and brine (100 mL), dried over anhydrous Na2SO4 and concentrated to afford the title compound.

Workup

  1. temperaturethen warmed to 60° C.
  2. stirringstirred for 3 hours
  3. washwashed with water (3×100 mL) and brine (100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b838b6771229468490cd20df4915de2b
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

Loading…