Methyl iodide → 2,3-Difluoroanisole

HRID 897140

Reaction equation

HRID 897140 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[C:10]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 808792,3-Difluorophenol

Product 1

HCID 27693442,3-DifluoroanisoleYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-Difluorophenol (4.55 g) was dissolved in DMF (25 mL) and was treated with powdered K2CO3 (6.0 grams) and the mixture was stirred at an ambient temperature for 10 minutes under nitrogen atmosphere. The mixture was treated with iodomethane (9.0 grams), and was stirred at room temperature for 18 hours. The reaction mixture was quenched with water and was extracted with ether. The ether extract was washed with water, dried (Na2SO4) and concentrated to afford 3.8 grams of title compound as amber oil. 1HNMR(CDCl3): δ 6.97(m, 1H), 6.78(m, 2H), 3.90(s, 3H). Step 2: 2,3-Difluoro-4-methoxybenzaldehyde.

Workup

  1. stirringwas stirred at room temperature for 18 hours
  2. customThe reaction mixture was quenched with water
  3. extractionwas extracted with ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f1b8da9c2eb14fada23a8be65ec8822b
Source dataset
uspto-grants-2005_07
Patent number
US06921767B2

Linked notes

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