Methyl iodide → Benzoic acid, 2-bromo-5-fluoro-, methyl ester
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:12][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:2]=1[Br:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-bromo-5-fluorobenzoic acid (7.92 g, 36.2 mmol) in N,N-dimethylformamide (75 mL) was added potassium carbonate (6.91 g, 50.0 mmol) as a solid in one portion at room temperature. The mixture was stirred for 5 minutes and iodomethane (6.39 g, 45.0 mmol) was added in one portion. The mixture was stirred at ambient temperature for 22 hours. The reaction mixture was partitioned between ethyl acetate and water. The aqueous portion was extracted with additional ethyl acetate (3×) and the combined organic extracts were washed successively with 10% potassium carbonate solution, water and brine. The organic portion was dried (Na2SO4) and concentrated to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.87 (s, 3H) 7.41 (td, J=8.56, 3.22 Hz, 1H) 7.65 (dd, J=8.99, 3.22 Hz, 1H) 7.81 (dd, J=9.16, 5.09 Hz, 1H); MS (+DCI/NH3) m/z 250.0 [M+NH4]+.
Workup
- stirringThe mixture was stirred at ambient temperature for 22 hours
- customThe reaction mixture was partitioned between ethyl acetate and water
- extractionThe aqueous portion was extracted with additional ethyl acetate (3×)
- washthe combined organic extracts were washed successively with 10% potassium carbonate solution, water and brine
- dry with materialThe organic portion was dried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5de3b6ba492440bb930031c699186b10
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846951B2
Reaction notes
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