Chlorosuccinimide → 4-chloro-1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 589039Notes

Reaction equation

[CH3:1][N:2]1[C:6]([B:7]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]2)=[CH:5][CH:4]=[N:3]1.[Cl:16]N1C(=O)CCC1=O>C1COCC1>[Cl:16][C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[B:7]1[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.3 g, 6.3 mmol), N-chlorosuccinimide (0.93 g, 7.0 mmol) and THF (6.6 mL) was stirred at 70° C. for 3 h. The mixture was extracted with EtOAc, dried and concentrated under reduced pressure. The sub-title compound was purified by chromatography on silica gel using 40% EtOAc in hexanes gave the desired compound, 1.456 g, 95%.

Workup

extractionThe mixture was extracted with EtOAc
customdried
concentrationconcentrated under reduced pressure
customThe sub-title compound was purified by chromatography on silica gel using 40% EtOAc in hexanes

Sources & evidence

ORD record: ord-e93378eb66b24210b1a01990076d660a
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227985B2

Reaction notes

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