1-Bromo-4-chloro-2-fluorobenzene → HCID 25212417, compound

HRID 1499106Notes

Reaction equation

HRID 1499106 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[CH:12]=[CH:11][NH:10][N:9]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1F>CS(C)=O>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[N:10]1[CH:11]=[CH:12][C:8]([CH3:7])=[N:9]1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[N:9]1[C:8]([CH3:7])=[CH:12][CH:11]=[N:10]1

Participants

6

Reactant 3

HCID 1372751-Bromo-4-chloro-2-fluorobenzeneHCID 23665647Potassium tert-butoxideHCID 178428694HCID 178428694, compound

Product 2

HCID 25212417HCID 25212417, compoundHCID 57609541HCID 57609541, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

Potassium t-butoxide (3.9 g, 0.33 mmol) was dissolved in DMSO (25 mL). To this solution was added 3-methylpyrazole (2.7 g, 0.33 mmol) and the reaction was heated at 50° C. for 30 min. 1-Bromo-4-chloro-2-fluorobenzene (4.6 g, 0.22 mmol) was then added and the reaction was stirred at 50° C. for 16 h. The reaction was cooled to RT and extracted with water and EtOAc, washed with brine, and dried over Na2SO4, filtered and concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtOAc/heptane) provided 1-(2-bromo-5-chlorophenyl)-3-methyl-1H-pyrazole and 1-(2-bromo-5-chlorophenyl)-5-methyl-1H-pyrazole as a 4:1 mixture that was used in the next step directly.

Workup

  1. temperatureThe reaction was cooled to RT
  2. extractionextracted with water and EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by normal phase silica gel column chromatography (EtOAc/heptane)

Sources & evidence

ORD record
ord-00ee8b2838d8438391b49ff0abd64f8c
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

Loading…