Bromine → HCID 67384609, compound

To a solution of 5-ethyl-3-phenyl-1H-pyrazole (10.0 g, 58.1 mmol) in DCM (150 mL) was added dropwise bromine (9.28 g, 58.1 mmol) at 0° C. The reaction was stirred at that temperature for 30 min and continued for 2 h at room temperature and then quenched with aqueous Na2SO3 solution (10% w/w, 10 mL). DCM was removed and the residue was extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a yellow liquid (9.5 g). LCMS m/z=250.9 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22 (t, J=7.58 Hz, 3H), 2.66 (q, J=7.58 Hz, 2H), 7.40-7.56 (m, 3H), 7.82 (d, J=7.58 Hz, 2H), 13.15 (s, 1H).

1. waitcontinued for 2 h at room temperature
2. customquenched with aqueous Na2SO3 solution (10% w/w, 10 mL)
3. customDCM was removed
4. extractionthe residue was extracted with EtOAc
5. washwashed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customThe residue was purified by silica gel column chromatography

ORD record

ord-90ebee7e06864ccf8614875a520662af

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012478B2