Dimethylformamide → 4-Fluoro-5-iodo-phthalic acid dimethyl ester
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[C:5](=[CH:9][C:10]=1[I:11])C(O)=O.[C:15](=[O:18])([O-])[O-].[K+].[K+].[CH3:21]I.CN([CH:26]=[O:27])C>>[CH3:15][O:18][C:26](=[O:27])[C:5]1[C:4](=[CH:3][C:2]([F:1])=[C:10]([I:11])[CH:9]=1)[C:12]([O:14][CH3:21])=[O:13]Participants
Conditions
- Temperature
- 35 °C
Procedure
To a stirred solution of 19.4 mmol 4-fluoro-5-iodo-phthalic acid in 60 ml DMF was added 58.1 mmol potassium carbonate. The mixture was then warmed to 35° C. and 38.7 mmol methyl iodide was added dropwise. The mixture was heated at 35° C. for 2 h and then at 60° C. for 4 h before being concentrated in vacuo. The residue was resuspended in ethyl acetate and water and the phases were separated The organic phase was washed sequentially with 0.5 M aq. sodium hydroxide solution and with brine, then dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluant ethyl acetate/heptane) to afford the title compound as an orange oil (53% yield). EI-MS (m/e): 338.0 (M+, 50%), 307.0 ([M−OMe]+, 100%).
Workup
- temperatureThe mixture was heated at 35° C. for 2 h
- concentrationat 60° C. for 4 h before being concentrated in vacuo
- customwater and the phases were separated The organic phase
- washwas washed sequentially with 0.5 M aq. sodium hydroxide solution and with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography on silica gel (eluant ethyl acetate/heptane)
Sources & evidence
- ORD record
- ord-5c6c39b716f64f0d8677ddf193cf139a
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557114B2
Reaction notes
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