HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 561489Generated: October 31, 2026
Diethyl Ether → 2-[(4-Chloro-2-fluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile
https://huagongshe.com/reaction/561489
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 2-(4-Chloro-2-fluorobenzoyl)cyclopropanecarbonitrile | HCID 58392490 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-[(4-Chloro-2-fluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile | HCID 58392222 | — |
Reaction Steps
1.01 g (26.6 mmol) of sodium borohydride were added to 5.40 g (24.1 mmol) of the compound from Example 130A in 99 ml of ethanol and 25 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 45 minutes. The reaction mixture was added to saturated aqueous ammonium chloride solution and diethyl ether, the phases were separated, the aqueous phase was extracted twice with diethyl ether, and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. 5.25 g (96% of theory) of a mixture of the diastereomers of the title compound were obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08063234B2 |
|---|
| Source dataset | uspto-grants-2011_11 |
|---|
| ORD ID | ord-332b290c8150456fbefdeb171e877268 |
|---|
| Source note | uspto-grants-2011_11 |
|---|