HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl Bromide → 1-Bromo-3-benzyloxy-4,5-difluorobenzene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl Bromide | HCID 7498 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-Bromo-2,3-Difluorophenol | HCID 2773307 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-Bromo-3-benzyloxy-4,5-difluorobenzene | HCID 57470601 | 0.1% |
Reaction Steps
A solution of DMF (100 mL), 5-bromo-2,3-difluorophenol (10 g, 47.85 mol), and K2CO3 (7.27 g, 52.63 mol) and benzyl bromide (9 g, 52.63 mol) were combined at 0° C. under N2. The solution was allowed to warm to rt and stirred overnight. H2O, Et3N (2 eq) and EtOAc (5000 mL) were added and the organic layer separated. The aqueous layer was washed with EtOAc (2×) and the combined organic fractions were washed with 1M HCl (2×), sat. aq. NaHCO3 (2×), dried, and concentrated. The crude product was purified by Biotage (gradient 100% hexanes-60% EtOAc/hexanes) to afford 10.08 g of product as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07902394B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-9499e05c84fc469890fe976704da6dab |
| Source note | uspto-grants-2011_03 |