Bromine → HCID 67385031, compound

3-(3-Phenyl-1H-pyrazol-5-yl)propan-1-ol (3.0 g, 14.83 mmol) was dissolved in dry DCM (40 mL) and THF (15 mL). The reaction was cooled in an ice bath and Br2 (1.146 mL, 22.25 mmol) pre-dissolved in DCM (10 mL) was added slowly dropwise: via addition funnel. The reaction was stirred for 2 h in an ice bath. The reaction was quenched by the addition of Na2SO3 (20 mL of 10% solution; the reaction went from reddish-brown to clear and some bubbling was observed). The reaction was extracted (100 mL each of H2O and DCM). The aqueous layer was extracted again with DCM (100 mL). The combined organic layer was back extracted again with H2O (200 mL). The organic layer was dried and concentrated to give the title compound (4.08 g) as a yellow solid. LCMS m/z=281.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.72-1.83 (m, 2H), 2.61-2.68 (m, 2H), 3.47 (t, J=6.44 Hz, 2H), 7.39 (t, J=7.33 Hz, 1H), 7.47 (t, J=7.45 Hz, 2H), 7.78 (d, J=7.07 Hz, 2H).

1. temperatureThe reaction was cooled in an ice bath
2. additionwas added slowly dropwise
3. additionvia addition funnel
4. customThe reaction was quenched by the addition of Na2SO3 (20 mL of 10% solution
5. extractionThe reaction was extracted (100 mL each of H2O and DCM)
6. extractionThe aqueous layer was extracted again with DCM (100 mL)
7. extractionThe combined organic layer was back extracted again with H2O (200 mL)
8. customThe organic layer was dried
9. concentrationconcentrated

ORD record

ord-07e7828d0eec4cfe9d0866634024fb39

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012478B2