Bromine → 2-(4-bromo-1h-pyrazol-1-yl)pyridine

HRID 2099500Notes

Reaction equation

HRID 2099500 reaction equation
[Br:1]Br.[N:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[N:4]1>CC(O)=O>[Br:1][C:6]1[CH:5]=[N:4][N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 53240862-(1H-pyrazol-1-yl)pyridine

Product 1

HCID 113451062-(4-bromo-1h-pyrazol-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (10.8 mL, 210 mmol) in AcOH (50 mL) was added carefully to a solution of 2-(1H-pyrazol-1-yl)pyridine (11 g, 70 mmol) in AcOH (100 mL) to give a brown precipitate. After stirring at ambient temperature for 3 h, the resulting reaction mixture was poured into ice and saturated aqueous Na2SO2O5 was added until the liquid phase became clear. The precipitate was removed by filtration and recrystallized from EtOH:H2O to give 2-(4-bromo-1H-pyrazol-1-yl)pyridine as beige crystals. 1H NMR (CD3Cl, 300 MHz) δ 8.61 (1H, s), 8.42 (1H, br. s), 7.94-7.96 (1H, m), 7.84 (1H, ddd), 7.69 (1H, s), 7.21-7.28 (1H, m). MS (ESI) 225 (M+H)+

Workup

  1. customto give a brown precipitate
  2. customthe resulting reaction mixture
  3. additionwas added until the liquid phase
  4. customThe precipitate was removed by filtration
  5. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-987b965aa21d4d8bb091e5feb0dd9d06
Source dataset
uspto-grants-2009_08
Patent number
US07569592B2

Reaction notes

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