Toluene → 1-Bromo-3-(1-phenylethenyl)benzene

HRID 1668696Notes

Reaction equation

HRID 1668696 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.[C:16]1(C)C=CC=CC=1.C1CCCCC1.C(OCC)(=O)C>O1CCCC1.[CH3-].C[Al]C.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Cl-].[Ti+4]>[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:4]([C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH2:16])[CH:3]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 705483-BromobenzophenoneHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 230831781-Bromo-3-(1-phenylethenyl)benzene

Reagents, catalysts & solvents 2

HCID 91617563mu-Methylene-mu-chlorobis(eta5-2,4-cyclopentadien-1-yl)(dimethylaluminum)titaniumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromobenzophenone (2.2 g, 8.5 mmol, 1 eq) in 20 mL of dry tetrahydrofuran at 0° C. under N2 atmosphere, was added a toluene solution of the Tebbe's reagent (17 mL of 0.5 M solution, 8.5 mmol, 1 eq.) and the mixture was allowed to warm to room temperature. The reaction mixture was examined after 20 min by TLC (cyclohexane/ethyl acetate 2%) which showed complete conversion to the desired product. Diethyl ether (50 mL) was added and some drops of NaOH 0.1 M aqueous solution was slowly added to quench the reaction. The mixture was dried over magnesium sulfate, passed through a pad of Celite and evaporated. The solid formed was triturated with cyclohexane and filtered; the solution was collected and concentrated under reduced pressure. The crude was purified by flash chromatography eluting with cyclohexane. 2.02 g of clean product was obtained as colorless liquid (yield: 91%).

Sources & evidence

ORD record
ord-76074725f7b74b019916cb0d779b2f77
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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