Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Allyl Alcohol | HCID 7858 | — |
| Reactant | 1-Chloro-2-iodobenzene | HCID 11993 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Catalyst | Tetrabutylammonium Chloride | HCID 70681 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-Chlorocinnamaldehyde | HCID 3014042 | 74% |
Reaction Steps
A mixture of 2.2 mL (18 mmol) of 2-chloroiodobenzene, 1.8 mL (27 mmol) of allyl alcohol, 81 mg (0.36 mmol) of Pd(OAc)2, 5.3 g (18 mmol) of Bu4NCl, and 3.8 g (45 mmol) of NaHCO3 in 50 mL of DMF is stirred under Ar2 at 30° C. for 24 h. Water is added and the mixture is extracted with EtOAc. The extract is washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (0-50% EtOAc in hexanes) provides 2.2 g (74%) of 3-(2-chlorophenyl)propenal.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08859814B2 |
|---|
| Source dataset | uspto-grants-2014_10 |
|---|
| ORD ID | ord-6790add3008d4712b95d944557dca659 |
|---|
| Source note | uspto-grants-2014_10 |
|---|
