Potassium Carbonate → 5-(4-Bromo-3-methyl-phenoxymethyl)-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-pyrazole

HRID 2261865Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].Br[CH2:11][C:12]1[N:16]([C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:24])[N:15]=[CH:14][C:13]=1[CH:25]([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][C:12]2[N:16]([C:17]3[C:18]([Cl:24])=[CH:19][CH:20]=[CH:21][C:22]=3[Cl:23])[N:15]=[CH:14][C:13]=2[CH:25]([CH3:27])[CH3:26])=[CH:4][C:3]=1[CH3:9]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-bromo-3-methyl-phenol (135 mg, 0.723 mmol) and 5-bromomethyl-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-pyrazole (210 mg, 0.603 mmol) in dimethylformamide (1.0 mL) is treated with potassium carbonate (84 mg, 0.603 mmol). The reaction mixture is heated at 80° C. for 60 minutes and cooled to room temperature. The mixture is loaded directly onto a silica gel column and purified with 25% EtOAc/Hexanes to provide 5-(4-bromo-3-methyl-phenoxymethyl)-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-pyrazole (0.258 g, 94%). ES/MS m/e (M+1) 454.8.

Workup

temperaturecooled to room temperature
custompurified with 25% EtOAc/Hexanes

Sources & evidence

ORD record: ord-6351d3036eee44f488b43efb2c97c72b
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846960B2

Reaction notes

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