Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Bromo-3-chlorobenzoic acid | HCID 33123 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 1463053-89-5 | HCID 73553325 | 65% |
Reaction Steps
To a solution of 2-bromo-3-chlorobenzoic acid (0.5 g, 2.12 mmol) in toluene (5 mL) were added Et3N (0.3 mL), DPPA (0.69 mL), and t-butanol (7.2 mL). The reaction mixture was heated at 100° C. overnight, cooled, and concentrated. This residue was extracted with ethyl acetate (20 mL). The organic phase was washed with aqueous HCl (5%, 20 mL), saturated NaHCO3, and saturated NaCl, was dried over anhydrous Na2SO4, and was concentrated to give the title compound as a solid (0.4 g, 65%). 1H NMR (400 MHz, CDCl3) δ 8.01 (1H, d, J=8.0 Hz), 7.19-7.12 (1H, m), 7.07-7.05 (2H, m), 1.46 (9H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365566B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-41325430f9764ba5be7915f8329b33a1 |
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| Source note | uspto-grants-2016_06 |
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