N-bromobutanimide → HCID 15220187, compound

HRID 583036Notes

Reaction equation

HRID 583036 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH3:19])[CH:13]=2)=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:19][C:14]1[CH:13]=[C:12]([C:3]2[C:2]([Cl:1])=[C:6]([O:7][CH:8]([F:9])[F:10])[N:5]([CH3:11])[N:4]=2)[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 15220186HCID 15220186, compound

Product 1

HCID 15220187HCID 15220187, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 20.0 g (65 mmol) of 4-chloro-5-difluoromethoxy-3-(4-chloro-3-methylphenyl)-1-methyl-1H-pyrazole (prepared as described in Example 2), 17.4 g (98 mmol) of N-bromosuccinimide and 200 ml of carbon tetrachloride was refluxed for 3 h under irradiation with a UV lamp. The solid constituents were then filtered off and were washed with a little methylene chloride. The solvent was removed under reduced pressure, and then the residue was purified by chromatography on silica gel (eluent: methylene chloride/hexane=8:2). Yield: 11.0 g; 1H-NMR (270 MHz, in CDCl3); δ [ppm]=7.98 (s, 1H), 7.80 (d, 1H), 7.46 (d, 1H), 6.70 (t, 1H), 4.64 (s, 2H), 3.87 (s, 3H).

Workup

  1. temperaturewas refluxed for 3 h under irradiation with a UV lamp
  2. filtrationThe solid constituents were then filtered off
  3. washwere washed with a little methylene chloride
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by chromatography on silica gel (eluent: methylene chloride/hexane=8:2)

Sources & evidence

ORD record
ord-bd9450d761ea4cb9bcd47a2908391e51
Source dataset
uspto-grants-1999_07
Patent number
US05928999

Reaction notes

Loading…