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

HRID 1918367Notes

Reaction equation

HRID 1918367 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-b685a36fd2da4f019ebe9fc78198d11a
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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