Hydrochloric Acid → HCID 70981527, compound

Temperature

90 °C

To a solution of 26 (7.38 g, 30.0 mmol) in CCl4 (90 mL) was added NBS (5.61 g, 31.5 mmol) and dibenzoyl peroxide (727 mg, 3.0 mmol). The reaction was heated at 90° C. in a sealed reaction vessel for about 4 h. Then DBU (6.73 mL, 45.0 mmol) in CH2Cl2 (15 mL) was added. The mixture was heated a reflux for 30 min, then a 1 M HCl solution was added. The layers were separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with a brine solution. The organic layer was then dried, filtered, and concentrated in vacuo. The crude product was adsorbed on ˜30 g of silica then run through a plug of silica with 40% EtOAc/hexanes to give 5.2 g of 27. 1H-NMR: 400 MHz, (CD3OH) δ: 7.25 (s, 1H), 6.69 (s, 1H), 2.40 (s, 3H). LCMS-ESI+: calc'd for C8H7BrNOS: 243.9 (M+H+). Found: 244.1 (M+H+).

1. temperatureThe mixture was heated
2. temperaturea reflux for 30 min
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with CH2Cl2
5. washThe combined organic layers were washed with a brine solution
6. customThe organic layer was then dried
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-1c6c6d8b50b84ef4954f45995244709e

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006229B2