Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | (1-(4-Bromophenyl)cyclopropyl)methanol | HCID 20252945 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1147531-61-0 | HCID 21257386 | 97.9% |
Reaction Steps
To a solution of DMSO (2.18 mL, 30.7 mmol) in dry DCM (15.0 mL) under nitrogen atmosphere, was added oxalyl chloride (1.21 mL, 14.2 mmol) at −78° C. The reaction mixture was stirred at this temperature for 30 min followed by addition of solution of (1-(4-bromophenyl)cyclopropyl)methanol (2.7 g, 11.8 mmol), in DCM (15.0 mL). The reaction mixture was stirred at −78° C. for 45 min followed by addition of triethylamine (8.2 mL, 59.2 mmol) and further stirring at same temperature for 15 min and then at r.t. for 15 min. The reaction mixture was diluted with DCM (100 mL) and water (100 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo to afford title compound (2.6 g, 93%) as viscous oil which was used as such in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09018249B2 |
|---|
| Source dataset | uspto-grants-2015_04 |
|---|
| ORD ID | ord-1c2bdd1d53bc4b1cb756721af62acdaf |
|---|
| Source note | uspto-grants-2015_04 |
|---|