Hydrochloric Acid → HCID 86714063, compound

Temperature

100 °C

To a solution of 3-allyl-4-(allylthio)-5-bromo-2-chlorobenzonitrile 94 (1.1 g, 3.35 mmol) in a mixture of EtOH (90 mL) and H2O (10 mL) was added NaOH (545 mg, 13.4 mmol). The reaction mixture was warmed up to 100° C., and stirred overnight. After reaction complete, the resulting solution was cooled down to room temperature. 1 N HCl solution was used for acidify reaction solution, and normal work-up with EtOAc was proceeded. Removal of volatile solvent was preceded by drying with MgSO4. Without further purification, crude acid was used for next step. The crude acid was dissolved in MeOH (50 mL), treated with SOCl2 (1 mL) provisionally. The reaction mixture was refluxed overnight and resulting solution was cooled down to room temperature and evaporated in vacuo. The residue was purified by silica gel chromatography to afford the desired product (710 mg, 63% overall yield) as a white solid.

1. customAfter reaction complete
2. temperaturethe resulting solution was cooled down to room temperature
3. customRemoval of volatile solvent
4. dry with materialby drying with MgSO4
5. customWithout further purification, crude acid
6. dissolutionThe crude acid was dissolved in MeOH (50 mL)
7. additiontreated with SOCl2 (1 mL) provisionally
8. temperatureThe reaction mixture was refluxed overnight
9. customresulting solution
10. temperaturewas cooled down to room temperature
11. customevaporated in vacuo
12. customThe residue was purified by silica gel chromatography

ORD record

ord-557a49fa30b34678b815b816c17fd7c6

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371303B2