HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 606790Generated: October 30, 2026
1-Bromo-3-chlorobenzene → 4-(3-Chlorophenyl)-2-methyl-3-butyn-2-ol
https://huagongshe.com/reaction/606790
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-Bromo-3-chlorobenzene | HCID 7928 | — |
| Reactant | 2-Methyl-3-butyn-2-ol | HCID 8258 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 4-(3-Chlorophenyl)-2-methyl-3-butyn-2-ol | HCID 23006374 | 94% |
Reaction Steps
Add triethylamine (75 mL), 1-bromo-3-chlorobenzene (24.1 g, 0.126 mol), and 2-methylbut-3-yn-2-ol (15 mL, 0.152 mol) to a degassed mixture of bis(triphenylphosphine)palladium (II) dichloride (49 mg, 7.1 10−5 mol) and copper (I) iodide (2.4 mg, 1.26 10−5 mol). Stir at 90° C. for 72 h. Cool the reaction mixture to room temperature. Filter, concentrate and dissolve in ethyl acetate. Wash with water and dry the organic phase over sodium sulfate. Filter, concentrate and purify the residue by silica gel chromatography, eluting with hexane:ethyl acetate 6:1, to give the title compound (23 g, 94%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07915424B2 |
|---|
| Source dataset | uspto-grants-2011_03 |
|---|
| ORD ID | ord-bf50737988824fb38228afe636909a32 |
|---|
| Source note | uspto-grants-2011_03 |
|---|
