Methyl iodide → Methyl 5-bromo-2-fluorobenzoate

HRID 1816971Notes

Reaction equation

HRID 1816971 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].CI.[C:14](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:14])=[O:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27363155-Bromo-2-fluorobenzoic acid

Product 1

HCID 21525435Methyl 5-bromo-2-fluorobenzoateYield 93.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-bromo-2-fluorobenzoic acid (25 g, 0.11 mol), methyl iodide (8.5 mL, 0.14 mol), and potassium carbonate (31 g, 0.23 mol) in DMF (200 mL) was heated to 50° C. for 18 hr. The cooled reaction mixture was diluted with EtOAc (200 mL) and the organic phase was washed with a saturated aqueous NaCl solution (4×). The organic phase was then dried over sodium sulfate and evaporated to dryness to give 24 g of methyl 5-bromo-2-fluorobenzoate as a yellow oil.

Workup

  1. customThe cooled reaction mixture
  2. washthe organic phase was washed with a saturated aqueous NaCl solution (4×)
  3. dry with materialThe organic phase was then dried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-737a3e8108924081bcbdc1601c47fb68
Source dataset
uspto-grants-2009_10
Patent number
US07598243B2

Reaction notes

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