Tributylphosphine → 5-(4-Bromo-3-methyl-phenoxymethyl)-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-[1,2,3]triazole

HRID 424781Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][OH:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[N:11]=[N:10]1.[Br:19][C:20]1[CH:25]=[CH:24][C:23](O)=[CH:22][C:21]=1[CH3:27].C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([O:15][CH2:14][C:13]2[N:9]([C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[N:10]=[N:11][C:12]=2[CH:16]([CH3:18])[CH3:17])=[CH:22][C:21]=1[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-yl]-methanol (300 mg, 1.05 mmol) in toluene (4 mL) are added 4-bromo-3-methyl-phenol (196 mg, 1.05 mmol) and tri-n-butylphosphine (394 μL, 1.58 mmol). The reaction mixture is cooled to 0° C. To the reaction mixture is added 1,1′-(Azocarbonyl)-dipiperidine (399 mg, 1.58 mmol) and the reaction mixture is warmed to room temperature. After 6 h, the reaction mixture is concentrated and the residue is chromatographed eluting with 10% to 20% EtOAc/hexanes to yield the title compound (324 mg, 68%). LC-ES/MS m/e 455.7 (M+1).

Workup

temperaturethe reaction mixture is warmed to room temperature
concentrationthe reaction mixture is concentrated
customthe residue is chromatographed
washeluting with 10% to 20% EtOAc/hexanes

Sources & evidence

ORD record: ord-8a7741ae88f74e548f0102b4d09b6275
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106077B2

Reaction notes

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