Methyl iodide → Methyl 3-bromo-5-fluoro-4-methoxybenzoate

HRID 1475778Notes

Reaction equation

HRID 1475778 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([OH:11])=[C:6]([Br:12])[CH:5]=1.[C:14]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH3:14])=[C:6]([Br:12])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57467610HCID 57467610, compound

Product 1

HCID 67076673Methyl 3-bromo-5-fluoro-4-methoxybenzoateYield 37.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.0 g of 3-Bromo-5-fluoro-4-hydroxy-benzoic acid methyl ester were dissolved using 50 ml of acetone. Then, 8.3 g of K2CO3 and 2.5 ml of CH3I were added and the reaction mixture stirred at room temperature for 48 h. The reaction mixture was then filtrated and evaporated. Chromatography on silica gel using EA/HEP 1:2 yielded 2.0 g of the title compound, oil.

Workup

  1. filtrationThe reaction mixture was then filtrated
  2. customevaporated

Sources & evidence

ORD record
ord-c9227e77ece548c1b9ca9d238395c022
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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