HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → HCID 67974355, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methyl 3-(bromomethyl)benzoate | HCID 517981 | — |
| Reactant | 3-Fluorophenylboronic acid | HCID 2733986 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 67974355 | HCID 67974355 | 50% |
Reaction Steps
A mixture of methyl 3-(bromomethyl)benzoate (0.500 g; 2.18 mmol), 3-fluorophenylboronic acid (0.334 g; 2.40 mmol), N,N-diisopropylethylamine (0.752 mL; 4.37 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with dichloromethane (0.178 g; 0.218 mmol) in water (1 mL) and dimethoxyethane (3 mL) was irradiated in a microwave oven at 130° C. for 15 minutes. The resulting mixture was partitioned between water and ethyl acetate and the phases were separated. The organic layer was washed with water and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to yield 0.265 g (50%) of methyl 3-(3-fluorobenzyl)benzoate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09266832B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-21c1e086a9f448e7ae37df90ce66acd2 |
| Source note | uspto-grants-2016_02 |