Methyl iodide → Methyl 5-bromo-2-fluorobenzoate
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
Product 1
Reagents, catalysts & solvents 2
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 24g of methyl 5-bromo-2-fluorobenzoate as a yellow oil. Step B:
Workup
- customThe cooled reaction mixture
- washthe organic phase was washed with a saturated aqueous NaCl solution (4×)
- dry with materialThe organic phase was then dried over sodium sulfate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-9b92c3b07dc741e993d3e90e0f09e9b9
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700591B2
Reaction notes
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