Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Bromine | HCID 24408 | — |
| Reactant | Sodium Bisulfite | HCID 23665763 | — |
| Reactant | HCID 66994464 | HCID 66994464 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | HCID 66995360 | HCID 66995360 | 66.3% |
Reaction Steps
Placed 4-(2-aminopyridin-3-yloxy)benzonitrile (13.95 g, 66.05 mmol) in acetic acid (50 mL) and cooled to 0° C. Slowly added bromine (4.229 mL, 82.56 mmol) and stirred for an hour. The reaction mixture was poured onto saturated sodium bisulfite and ice. Extracted with dichloromethane three times, washed with 2N NaOH, water, brine, dried, and concentrated. Purified by MPLC eluting with 3:2 hexane:ethyl acetate to afford the title compound (12.7 g, 66.28% yield) as a light yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08883828B2 |
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| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-985e0aceb034479083ee37012664e692 |
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| Source note | uspto-grants-2014_11 |
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