N-bromobutanimide → 4-bromo-1-(4-methoxyphenyl)-1H-pyrazole

HRID 537528Notes

Reaction equation

HRID 537528 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1.[Br:14]N1C(=O)CCC1=O>O1CCCC1>[Br:14][C:12]1[CH:11]=[N:10][N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 122381311-(4-Methoxyphenyl)-1H-pyrazole

Product 1

HCID 534180304-bromo-1-(4-methoxyphenyl)-1H-pyrazoleYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-methoxyphenyl)-1H-pyrazole (7.2 g, 0.042 mol) in tetrahydrofuran (100 mL) was added N-bromosuccinimide (7.3 g, 0.042 mol). The reaction was stirred at room temperature for 3 hours. The reaction was concentrated and purification by column chromatography gave 4-bromo-1-(4-methoxyphenyl)-1H-pyrazole (8.9 g, 84%) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 7.83 (s, 1H), 7.63 (s, 1H), 7.52 (d, J=8.8 Hz, 2H), 6.97 (d, J=8.8 Hz, 2H), 3.84 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurification by column chromatography

Sources & evidence

ORD record
ord-f5bdaa7da7b64fb1a82fefda6166b407
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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