Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | HCID 67211153 | HCID 67211153 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 67211302 | HCID 67211302 | 73.7% |
Reaction Steps
5-(Hydroxymethyl)-2-(trifluoromethoxy)benzonitrile (0.150 g, 0.691 mmol) was taken up in toluene (2 mL) and thionyl chloride (0.303 mL, 4.14 mmol) was added. The mixture was heated at 75° C. for 15 min. Water was added and the mixture was extracted with hexanes (2×75 mL). The organics were treated with aqueous NaHCO3. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated to give the title compound as a colorless oil (120 mg). LCMS m/z=236.2 [M+H]+. 1H NMR (500 MHz, CDCl3) δ ppm 1.98 (s, 1H), 4.52 (s, 2H), 7.32-7.34 (m, 1H), 7.59-7.62 (m, 1H), 7.68 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09126932B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-6c0202236a844b498acb2920efdf7473 |
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| Source note | uspto-grants-2015_09 |
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