HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl 3-bromobenzoate → (E)-3-(2-Cyclohexyl-1-hydroxymethyl-vinyl)-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl 3-bromobenzoate | HCID 12070 | — |
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol | HCID 67084598 | — |
| Catalyst | HCID 178420553 | HCID 178420553 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (E)-3-(2-Cyclohexyl-1-hydroxymethyl-vinyl)-benzoic acid methyl ester | HCID 67084697 | 74.7% |
Reaction Steps
Following the method of example 46a, Suzuki coupling of 3-bromo-benzoic acid methyl ester (1.05 g, 4.88 mmol) with (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.48 g, 5.56 mmol) in the presence of tetrakis(triphenylphosphino)palladium(0) (0.32 g, 0.28 mmol) and cesium fluoride (2.2 g, 14 mmol) in dioxane (15 mL) gives the title compound (1.0 g). MS (m/e): 257 (M+H−H2O).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07576108B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-6c6e775a4da64986b1d0d02d4755931c |
| Source note | uspto-grants-2009_08 |