1,4-Dibromo-2-fluorobenzene → 1-(2,5-dibromophenyl)-3-methyl-1H-pyrazole

HRID 1499100

Reaction equation

HRID 1499100 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]([Br:20])=[CH:16][C:15]=1F>CS(C)=O>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=1[N:10]1[CH:11]=[CH:12][C:8]([CH3:7])=[N:9]1

Participants

5

Reactant 3

HCID 1370041,4-Dibromo-2-fluorobenzeneHCID 23665647Potassium tert-butoxideHCID 178428694HCID 178428694, compound

Product 1

HCID 1179420861-(2,5-dibromophenyl)-3-methyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

Potassium t-butoxide (16.3 g, 145 mmol) was dissolved in DMSO (100 mL). To this solution was added 3-methylpyrazole (10.4 g, 120 mmol) and the reaction was heated at 50° C. for 30 min. 1,4-Dibromo-2-fluorobenzene (31 g, 120 mmol) was then added and the reaction stirred at 50° C. for 16 h. The reaction was cooled to RT and extracted with water and EtOAc, washed with brine, dried over Na2SO4, and then filtered and concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtOAc/heptane) provided 1-(2,5-dibromophenyl)-3-methyl-1H-pyrazole.

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-901aa5158b204eef8b30ba18c6c6783d
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Linked notes

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