Methyl iodide → 2-Bromo-5-fluoroanisole

HRID 1372264Notes

Reaction equation

HRID 1372264 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].IC.[C:12](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH3:12]

Participants

6

Procedure

To a mixture of 2-bromo-5-fluorophenol (10 g, 50.8 mmol) and iodomethane (11.2 g, 78.7 mmol) in dimethylformamide (100 mL) was added potassium carbonate (10.9 g, 79 mmol) and the mixture stirred at room temperature for 3 hrs. The mixture was diluted with water (100 mL) and extracted with ether (50 mL×3). The combined extracts were washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain 11.3 g of 1-bromo-4-fluoro-2-methoxybenzene as an amber colored oil.

Workup

  1. extractionextracted with ether (50 mL×3)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aeffdcbe072d488aa0962013476f8370
Source dataset
uspto-grants-2007_01
Patent number
US07157447B2

Reaction notes

Loading…