HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-bromobutanimide → Methyl 5-(bromomethyl)thiophene-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | Methyl 5-methyl-2-thiophenecarboxylate | HCID 580756 | — |
| Catalyst | Benzoyl Peroxide | HCID 7187 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | Methyl 5-(bromomethyl)thiophene-2-carboxylate | HCID 11424851 | 100% |
Reaction Steps
Add freshly recrystallised NBS (323.8 g, 1.81 mol) to a solution of methyl-5-methylthiophene-2-carboxylate (258 g, 1.65 mol) in chloroform (2.6 L) at room temperature, and stir. Add benzoyl peroxide (3.99 g, 0.016 mol) and heat the reaction mixture to reflux for 7 hours. Cool the reaction mixture to ambient temperature and filter through diatomaceous earth. Wash the filter cake with chloroform (250 ml). Collect the organic layers and remove the solvent to give the title compound (388 g, 100%), which is used without further purification. ESI (m/z) 236(M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08431706B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-d03ffbcf1aae4812ac25c4960793156c |
| Source note | uspto-grants-2013_04 |