Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Cyclopropanemethanol | HCID 75644 | — |
| Reactant | 5-Bromo-2-fluorobenzonitrile | HCID 2724900 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71295195 | HCID 71295195 | 92.6% |
Reaction Steps
Sodium hydride, 60% suspension in oil (3.6 g, 0.09 mol), is added to a solution of cyclopropylmethanol (6.49 g, 0.09 mol) in dry DMF (200 ml) at 0° C. under nitrogen. After 30 min at 0° C., 5-bromo-2-fluorobenzonitrile (12.0 g, 0.06 mol) in dry DMF (50 ml) is added, and the reaction is stirred at 50° C. for 16 h. Ice-water (200 ml) is added to the reaction mixture, which is then extracted with ethyl acetate (2×200 ml). The organic phases are washed with water (2×200 ml) and saturated sodium chloride solution (1×200 ml) and dried over sodium sulfate. After removal of the solvent, the crude product is purified by chromatography, giving 14 g of a yellow oil;
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08969335B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-349699eb17d144dab713106e68d0929d |
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| Source note | uspto-grants-2015_03 |
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