HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → (R)-1-(2-Fluorophenyl)ethanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | o-Fluoroacetophenone | HCID 96744 | — |
| Reactant | (3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaborole | HCID 2734713 | — |
| Reactant | (Dimethyl sulfide)trihydroboron | HCID 12423031 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (R)-1-(2-Fluorophenyl)ethanol | HCID 2779054 | — |
Reaction Steps
2′-Fluoroacetophenone (25 g, 180 mmol) and (S)-(−)-2-methyl-CBS-oxazaborolidine (6.02 g, 22 mmol) were combined in THF (200 mL). Borane methyl sulfide complex (2M in THF; 59.4 mL, 119 mmol) was added over 20 minutes, and the reaction was stirred at room temperature for 30 minutes. Methanol was added, and the mixture was worked-up with dichloromethane and water. The organic layer was concentrated to give (R)-1-(2-fluoro-phenyl)-ethanol in 90.6% e.e.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08048902B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-40b449cf7a884dc0980984aac83cb3fe |
| Source note | uspto-grants-2011_11 |