Methyl iodide → 2-Chloro-6-fluoroanisole

HRID 500599Notes

Reaction equation

HRID 500599 reaction equation
CI.[C:3](=[O:6])([O-])[O-].[K+].[K+].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1O>O1CCCC1>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1[O:6][CH3:3]

Participants

5

Procedure

Methyl iodide (850 μl, 13.646 mmol) and potassium carbonate (943 mg, 6.824 mmol) were added to 2-chloro-6-fluorophenol (1.0 g, 6.824 mmol) in tetrahydrofuran (10 ml) and the mixture was stirred at room temperature for 3 hours. The reaction mixture was partitioned between diethyl ether (50 ml) and water (50 ml). The organic phase was extracted and further washed with water (2×20 ml) then dried over sodium sulphate and concentrated in vacuo to afford the title compound as a colourless liquid in 94% yield, 1.03 g.

Workup

  1. customThe reaction mixture was partitioned between diethyl ether (50 ml) and water (50 ml)
  2. extractionThe organic phase was extracted
  3. washfurther washed with water (2×20 ml)
  4. dry with materialthen dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5a6a825cd644778bc7a654480f190f0
Source dataset
uspto-grants-2010_08
Patent number
US07772223B2

Reaction notes

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