Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 4-Bromo-3-fluorobenzotrifluoride | HCID 142414 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 89813599 | HCID 89813599 | 36% |
Reaction Steps
A microwave vial charged with potassium phosphate (0.533 g, 2.51 mmol), 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (0.610 g, 2.51 mmol) and 1 mL dioxane, was treated with morpholine (0.437 ml, 5.02 mmol) and was heated to 150° C. in a microwave reactor for one hour. LC/MS showed mostly starting material, so the reaction mixture was treated with 1 mL DMF and was heated to 150° C. in an oil bath overnight. LC/MS showed product, so the reaction mixture was diluted with DCM, filtered through a syringe filter, and concentrated. Purification of the resulting residue by silica gel column chromatography (0 to 50% EtOAc/heptane) gave 4-(2-bromo-5-(trifluoromethyl)phenyl)morpholine (0.280 g, 0.903 mmol) as a clear oil. [M+H]+=312.0
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051311B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-8836d701547545d09b8dcd4542e9f5a6 |
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| Source note | uspto-grants-2015_06 |
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