HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → 5-(2-bromoethyl)-4-methylthiazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | 1-(4-Methyl-1,3-thiazol-5-yl)ethan-1-ol | HCID 581758 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-(2-bromoethyl)-4-methylthiazole | HCID 204187 | 62.4% |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
A solution of 1 g (7 mmol) of 4-methyl-5-thiazolylethanol in 15 mL of dichloromethane is cooled to 0° C. under argon. In a first stage, 1.8 g (7 mmol) of triphenylphosphine are added. Next, 1.30 g (7 mmol) of N-bromosuccinimide are added portionwise over 5 minutes. After stirring for 2 hours at 0° C., the solvent is evaporated off under vacuum. The residue obtained is purified by chromatography on silica gel (eluent: 50/50 EtOAc/heptane) to give 900 mg of 5-(2-bromoethyl)-4-methylthiazole, the characteristics of which are as follows:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321790B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-1d938bc7b16142089427a1ea97ab4627 |
| Source note | uspto-grants-2016_04 |