Phenethyl bromide → HCID 58710082, compound

HRID 624005Notes

Reaction equation

HRID 624005 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Br[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazole

Product 1

HCID 58710082HCID 58710082, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-nitro-1H-pyrazole (1.50 g, 12.87 mmol) in MeCN (30 mL), (2-bromoethyl)benzene (1.97 mL, 14.15 mmol) and Cs2CO3 (4.61 g, 14.15 mmol) was added. The resulting mixture was refluxed (80° C.) for 1.5 h, then the reaction mixture was allowed to reach rt. The mixture was diluted with DCM, filtered, the filter cake was washed with DCM and the filtrate was concentrated in vacuo to obtain 4-nitro-1-phenethyl-1H-pyrazole as a beige solid which was used in the next step without further purification. LC-MS conditions A: tR=0.92 min; [M+H]+=217.97.

Workup

  1. customto reach rt
  2. filtrationfiltered
  3. washthe filter cake was washed with DCM
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5f56696150e8430295920546005f76cd
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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