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

HRID 1845552
Notes
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Reaction equation

HRID 1845552 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 578265674-bromo-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic Acid

Product 1

HCID 578266064-bromo-5-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic AcidYield 0.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

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

Sources & evidence

ORD record
ord-5101d2c3cebc4950b6cb1dbd4a3debf8
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946278B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes