Potassium tert-butoxide → 1,3-Dichloro-5-(3,3-dichloro-allyloxy)-2-[2-(4-trifluoromethyl-phenoxymethyl)-allyloxy]-benzene

HRID 1869143Notes

Reaction equation

[CH3:1]C([O-])(C)C.[K+].[Cl:7][C:8]1[CH:29]=[C:28]([O:30][CH2:31][CH:32]=[C:33]([Cl:35])[Cl:34])[CH:27]=[C:26]([Cl:36])[C:9]=1[O:10][CH2:11][C:12](=O)[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:29]=[C:28]([O:30][CH2:31][CH:32]=[C:33]([Cl:34])[Cl:35])[CH:27]=[C:26]([Cl:36])[C:9]=1[O:10][CH2:11][C:12]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:17][CH:16]=1)=[CH2:1]

Participants

Conditions

Temperature: 50 °C

Procedure

189 mg of potassium tert-butylate and 532 mg of methyltriphenylphosphonium bromide are heated in 8 ml of toluene for 3 hours at 80° C. The reaction mixture is cooled to 50° C. and a solution of 500 mg of 1-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-3-(4-tri-fluoromethyl-phenoxy)-propan-2-one in 5 ml of toluene is added in the course of 5 minutes. After 2 hours at 80° C., the reaction mixture is filtered, diluted with ethyl acetate and washed with water. After concentration of the organic phase and purification over silica gel, the title compound is obtained.

Workup

filtrationthe reaction mixture is filtered
additiondiluted with ethyl acetate
washwashed with water
customAfter concentration of the organic phase and purification over silica gel

Sources & evidence

ORD record: ord-9b272468c2e541609d40f113bdd2af65
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638514B2

Reaction notes

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