Diethyl Ether → 2'-Chloro-2-((3,5-bis(trifluoromethyl)phenyl) methyloxy)acetophenone

HRID 976037Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C([Sn](CCCC)(CCCC)[CH2:16][O:17][CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=1)CCC.C(OCC)C.[F-].[K+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](=[O:5])[CH2:16][O:17][CH2:18][C:19]1[CH:20]=[C:21]([C:29]([F:30])([F:31])[F:32])[CH:22]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:24]=1

Participants

Conditions

Temperature: 70 °C

Procedure

2-Chlorobenzoyl chloride (1.27 ml), tri-n-butyl-((3,5-bis(trifluoromethyl)phenyl)methyloxymethyl)tin (part (a), 6.2 g) and benzylchlorobis(triphenylphosphine)palladium (II) (80 mg) were dissolved in chloroform (10 ml) and the solution heated to 70° C. for 36 hours. On cooling diethyl ether and saturated aqueous potassium fluoride were added and this solution filtered through a pad of Hyflo. The organic layer was washed with water, dried (MgSO4) and reduced in vacuo giving a residue which was purified by chromatography on silica gel to give 2'-chloro-2-((3,5-bis(trifluoromethyl)phenyl) methyloxy)acetophenone, 1H NMR (360MHz, CDCl3) δ 7.79 (3H, bs, bis(CF3) aryl CH2,4,6), 7.54-7.26 (4H, m, aryl), 4.75 (2H, s), 4.76 (2H, s).

Workup

additionwere added
filtrationthis solution filtered through a pad of Hyflo
washThe organic layer was washed with water
dry with materialdried (MgSO4)
customgiving a residue which
customwas purified by chromatography on silica gel

Sources & evidence

ORD record: ord-c142067de2bc43649bfaea28bb9de951
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05610183

Reaction notes

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