Benzoyl Peroxide → HCID 59239995, compound

HRID 1672990Notes

Reaction equation

HRID 1672990 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])[N:7]=1)=[O:5])[CH3:2].[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][Br:20])[N:8]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 57470283HCID 57470283, compound

Product 1

HCID 59239995HCID 59239995, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A 2 L flask was charged with 44.6 g of 1-(2,6-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester (133 mmol), 28.43 g of N-bromosuccinimide, 0.80 g of benzoyl peroxide and 1 L of carbon tetrachloride. The resulting solution was placed under a high intensity lamp for 2 hours. The resulting solution was allowed to cool to room temperature, filtered through a pad of celite. The filtrate was then concentrated in vacuo and the crude bromide was passed through a plug of silica using 40% EtOAc:hexane and recrystallized from heptane-ethanol to afford 5-bromomethyl-1-(2,6-dichlorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester was recovered as a tan solid (19.3 g, 38%); 1H NMR (400 MHz, CDCl3): δ 7.45 (m, 4H), 7.05 (s, 1H), 6.77 (s 0.2H starting material), 4.43 (q, J=7.07 Hz 2H), 4.27 (s, 2.16H), 2.14 (s, 0.6H starting material); 1.41 (t, J=7.07 Hz 3H), MS (ES): 399 [M+Na]+.

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationThe filtrate was then concentrated in vacuo
  3. customhexane and recrystallized from heptane-ethanol

Sources & evidence

ORD record
ord-496ecc7aa5a246de8888c6ed7f69e4b7
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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