HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 4-(azidomethyl)-2-chlorobenzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | Methyl 2-chloro-4-(hydroxymethyl)benzoate | HCID 19780655 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 4-(azidomethyl)-2-chlorobenzoate | HCID 57461226 | 98% |
Reaction Steps
A solution of 2-chloro-4-(hydroxymethyl)benzoic acid, methyl ester (11.09 g, 55.3 mmol), diphenylphosphoryl azide (22.58 g, 82.0 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (8.57 g, 56.3 mmol) in tetrahydrofuran was stirred overnight at room temperature. Silica gel was added and the solvent was evaporated. The residue was chromatographed (10% ethyl acetate/hexanes) to give 4-(azidomethyl)-2-chlorobenzoic acid, methyl ester (12.17 g, 98%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06331640B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-cdc7067a73e640a9b4d9ea4b5c70f2e3 |
| Source note | uspto-grants-2001_12 |