Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | tert-Butyl methyl ether | HCID 15413 | — |
| Reactant | 1-Bromo-5-chloro-4-fluoro-2-iodobenzene | HCID 50998080 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 77174822 | HCID 77174822 | — |
Reaction Steps
A solution of 1 mmol of n-butyllithium (1N in hexane) is added dropwise to a solution of 1 mmol of 1-bromo-5-chloro-4-fluoro-2-iodo-benzene in 20 ml of tetrahydrofuran cooled to −78° C. After the addition, 1.1 mmol of N,N-dimethylformamide is added and the mixture is allowed to warm to room temperature. 100 ml of tert-butylmethyl ether then 20 ml of water are added. The organic phase is separated, washed with 20 ml of brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title compound which is identified based on the Rf value.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08324235B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-9bd65d72eb75415199fdea3ad293c960 |
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| Source note | uspto-grants-2012_12 |
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