N-bromobutanimide → 1-Bromomethyl-4-chloro-3-(2,4-dichloro-5-(dibromomethyl)phenyl)-5-difluoromethoxy-1H-pyrazole

HRID 1599993Notes

Reaction equation

HRID 1599993 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([CH:18]([Br:20])[Br:19])[C:15]([Cl:21])=[CH:14][C:13]=2[Cl:22])=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9].[Br:23]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[Br:23][CH2:11][N:5]1[C:6]([O:7][CH:8]([F:9])[F:10])=[C:2]([Cl:1])[C:3]([C:12]2[CH:17]=[C:16]([CH:18]([Br:20])[Br:19])[C:15]([Cl:21])=[CH:14][C:13]=2[Cl:22])=[N:4]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 150305713-(5-dibromomethyl-2,4-dichlorophenyl)-4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole

Product 1

HCID 189261781-Bromomethyl-4-chloro-3-(2,4-dichloro-5-(dibromomethyl)phenyl)-5-difluoromethoxy-1H-pyrazoleYield 28.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 6 g (12 mmol) of 4-chloro-3-(2,4-dichloro-5-(di-bromomethyl)phenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole and 6.4 g (36 mmol) of N-bromosuccinimide in 800 ml of tetrachloromethane was irradiated for 2 hours with a 150 W high-pressure mercury lamp and a UV lamp. The solids were then removed by filtration, and the filtrate was concentrated. Silica gel chromatography of the residue (eluent: hexane/ethyl acetate=4:1) gave 2 g of the target product. 1H-NMR (250 MHz, in CDCl3): δ [ppm]=5.87(s,2H); 6.82(t,1H); 7.03(s,1H); 7.52(s,1H); 8.08(s,1H).

Workup

  1. customThe solids were then removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e15aff7926834d98b9f53fa946966c4d
Source dataset
uspto-grants-1998_04
Patent number
US05744426

Reaction notes

Loading…