Chlorosuccinimide → 4-bromo-5-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic Acid

HRID 1961180Notes

Reaction equation

[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[C:12]([C:21]([OH:23])=[O:22])[S:13][C:14]=1[C:15]1[N:19]([CH3:20])[N:18]=[CH:17][CH:16]=1>O1CCCC1>[Br:9][C:10]1[CH:11]=[C:12]([C:21]([OH:23])=[O:22])[S:13][C:14]=1[C:15]1[N:19]([CH3:20])[N:18]=[CH:17][C:16]=1[Cl:1]

Participants

Conditions

Temperature: 70 °C

Procedure

N-chlorosuccinimide (NCS) (299 mg, 2.194 mmol) was added in portions to a 30 mL sealed tube reactor containing 4-bromo-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid (503 mg, 1.23 mmol) in tetrahydrofuran (THF) (6 mL) at room temperature. The mixture was heated to 70° C. for 2 hours. Upon completion, the reaction mixture was partitioned between CHCl3 and H2O, the organic layer dried with Na2SO4, solvents removed by vacuum distillation affording the title compound (0.54 mg, quant.) which was used without further purification. LC-MS (ES) m/z=321 (M+H)+

Workup

customsealed tube reactor
customUpon completion, the reaction mixture was partitioned between CHCl3 and H2O
dry with materialthe organic layer dried with Na2SO4, solvents
customremoved by vacuum distillation

Sources & evidence

ORD record: ord-827c7bb6bd8a44839ca929074f365bfc
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410158B2

Reaction notes

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