HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → (E)-2-Chloro-4-(2-cyclohexyl-1-hydroxymethyl-vinyl)-benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Bromo-2-chlorobenzenesulfonamide | HCID 2734764 | — |
| Reactant | (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol | HCID 67084598 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (E)-2-Chloro-4-(2-cyclohexyl-1-hydroxymethyl-vinyl)-benzenesulfonamide | HCID 67084477 | 109.8% |
Reaction Steps
According to example 26b, reaction of 4-bromo-2-chloro-benzenesulfonamide (1.0 g, 3.7 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (271 mg, 0.37 mmol), (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.5 g, 5.5 mmol) and aqueous sodium carbonat solution (2 M, 3.60 mL, 7.40 mmol) in 15 mL DMF at 80° C. and purification via column chromatography on silica gel, eluting with a gradient from 70:30 to 50:50 hexane:ethyl acetate affords the title compound as an oil (1.34 g). MS (m/e): 312 [(M−H2O)+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07576108B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-5a759fa633e345ecbbd421a9686375cb |
| Source note | uspto-grants-2009_08 |