HuagongsheHuagongshe Chemistry Print Report · For research reference only
Azobisisobutyronitrile → Methyl 4-(bromomethyl)-3-chlorothiophene-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Azobisisobutyronitrile | HCID 6547 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | Methyl 3-chloro-4-methylthiophene-2-carboxylate | HCID 2777567 | — |
| Solvent | Carbon Tetrachloride | HCID 5943 | — |
| Product | Methyl 4-(bromomethyl)-3-chlorothiophene-2-carboxylate | HCID 18376575 | 39% |
Reaction Steps
A solution of methyl 3-chloro-4-methylthiophenecarboxylate (10 g, 53 mmol), N-bromosuccinimide (9.4 g, 53 mmol) and azo-bis-(isobutyronitrile) (860 mg, 5.3 mmol) in carbon tetrachloride (300 ml) was heated at reflux for 18 h. The mixture was filtered and reduced. Chromatography (10% EtOAc/90% hexanes) afforded methyl 4-bromomethyl-3-chlorothiophene-2-carboxylate (5.5 g, 39%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07365065B2 |
| Source dataset | uspto-grants-2008_04 |
| ORD ID | ord-c153adddf8964eab96439cd0dfd244d4 |
| Source note | uspto-grants-2008_04 |