HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → 3-(4-Bromophenyl)-3-methyloxetane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | 2-(4-Bromophenyl)-2-methylpropane-1,3-diol | HCID 12457149 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 3-(4-Bromophenyl)-3-methyloxetane | HCID 59206220 | 42% |
Reaction Steps
2-(4-Bromophenyl)-2-methylpropane-1,3-diol (100 mg, 0.41 mmol), triphenyl phosphine (210 mg, 0.82 mmol), and diisopropyl azodicarboxylate (160 μL, 0.82 mmol) were combined in toluene (2 mL) and irradiated in the microwave at 140° C. for 10 minutes. The mixture was directly purified by silica gel chromatography eluting with 0-20% ethyl acetate in hexanes to give 3-(4-bromophenyl)-3-methyloxetane (39 mg, 42%) 1H NMR (400 MHz, DMSO-d6) δ 7.38-7.34 (m, 2H), 7.26-7.22 (m, 2H), 4.82-4.80 (m, 2H), 4.55-4.54 (m, 2H), 1.62 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07691902B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-e6e47d854c3242e792753956df916eb1 |
| Source note | uspto-grants-2010_04 |