Potassium tert-butoxide → 1,3-Dichloro-5-(3,3-dichloro-allyloxy)-2-[4-(4-fluoro-phenyl)-pent-4-enyloxy]-benzene

HRID 1869150Notes

Reaction equation

[CH3:1]C([O-])(C)C.[K+].[Cl:7][C:8]1[CH:26]=[C:25]([O:27][CH2:28][CH:29]=[C:30]([Cl:32])[Cl:31])[CH:24]=[C:23]([Cl:33])[C:9]=1[O:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=O>[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:26]=[C:25]([O:27][CH2:28][CH:29]=[C:30]([Cl:32])[Cl:31])[CH:24]=[C:23]([Cl:33])[C:9]=1[O:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[CH2:1]

Participants

Conditions

Temperature: 80 °C

Procedure

84 mg of potassium tert-butylate and 236 mg of methyltriphenylphosphonium bromide are stirred in 6 ml of toluene for 3 hours at 80° C. 200 mg of 4-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-1-(4-fluoro-phenyl)-butan-1-one in 2 ml of toluene are then added and the mixture is stirred for a further 2 hours at 80° C. The reaction mixture is cooled and filtered and the filtrate is concentrated. After purification over silica gel, the title compound is obtained.

Workup

temperatureThe reaction mixture is cooled
filtrationfiltered
concentrationthe filtrate is concentrated
customAfter purification over silica gel

Sources & evidence

ORD record: ord-5f4aced13c134e37b8a19880b9a4e70b
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638514B2

Reaction notes

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