Water → 4-Bromo-3-phenyl-1H-pyrazole

HRID 1895129Notes

Reaction equation

HRID 1895129 reaction equation
[C:1]1([C:7]2[CH:11]=[CH:10][NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Br:19])C(=O)C1.O>CN(C=O)C>[Br:19][C:11]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][NH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 178420101HCID 178420101, compound

Product 1

HCID 1784194634-Bromo-3-phenyl-1H-pyrazoleYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-phenyl-1H-pyrazole (4.08 g, 28.3 mmol) and NBS (5.04 g, 28.3 mmol) in DMF (40 mL) was stirred for 1 h at room temperature. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was recrystallized from hexane/AcOEt to give the title compound (5.84 g, 93% yield) as a white solid: mp 114-116° C.; 1H NMR (300 MHz, CDCl3): δ ppm 7.39-7.50 (3H, m), 7.64 (1H, s), 7.77 (2H, d, J=6.8 Hz), 10.73 (1H, brs).

Workup

  1. extractionextracted with AcOEt
  2. washThe extract was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from hexane/AcOEt

Sources & evidence

ORD record
ord-9b9320d681a6489fa8d7c776af6903ef
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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