Pyrazole → 1-(2-(4-Bromophenoxy)ethyl)-1H-pyrazole

HRID 1054897Notes

Reaction equation

HRID 1054897 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10]Br)=[CH:4][CH:3]=1.[NH:12]1[CH:16]=[CH:15][CH:14]=[N:13]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 877972-Bromoethyl p-bromophenyl ether

Product 1

HCID 467394231-(2-(4-Bromophenoxy)ethyl)-1H-pyrazoleYield 104.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 1-bromo-4-(2-bromoethoxy)benzene (1.00 g, 3.57 mmol), pyrazole (0.360 g, 5.36 mmol) and cesium carbonate (1.75 g, 5.36 mmol) in acetonitrile (10 mL) was heated at 80° C. and stirred for 2 hours. The reaction mixture was filtered. The filtrate was concentrated in vacuo to give a white solid, which was purified by silica gel chromatography to give the title compound (1.0 g, 100%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.56 (d, 1H) 7.54 (d, 1H) 7.35 (d, 2H), 6.74 (d, 2H), 6.26 (m, 1H), 4.53 (t, 2H), 4.30 (t, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customto give a white solid, which
  4. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-b2e4bf71c69648a0b97e3b382708e6be
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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