Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Chlorophenol | HCID 4684 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,4,5-Trifluorobenzenesulfonyl chloride | HCID 2776979 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 89544319 | HCID 89544319 | 98% |
Reaction Steps
To a stirred solution of 4-chlorophenol (13.94 g, 108 mmol) in tetrahydrofuran (400 mL) at ambient temperature was added triethylamine (30.2 mL, 216 mmol). The mixture was stirred at ambient temperature for 10 minutes and cooled to 0° C. 2,4,5-Trifluorobenzenesulfonyl chloride (25.00 g, 108 mmol) was added and the reaction mixture was stirred for 1 h at ambient temperature and diluted with ethyl acetate (600 mL) and water (200 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford 4-chlorophenyl 2,4,5-trifluorobenzenesulfonate as a colorless liquid in 98% yield (34.4 g): 1H NMR (300 MHz, DMSO-d6) δ8.18-7.96 (m, 2H), 7.50 (d, J=7.2 Hz, 2H), 7.19 (d, J=7.2 Hz, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365578B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-4c3d64d9a1b54b64a817b5ace8bc3d58 |
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| Source note | uspto-grants-2016_06 |
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