Benzene → Biphenyl
Reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7]1([Li])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OC(N[C@H](C(O)=O)C)=O)C.C1([Mg]Br)C=CC=CC=1>CCOCC.O1CCCC1>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The techniques which resulted in successful amido acylation of benzene using phenyllithium were next applied to the Grignard reaction. N-ethoxycarbonylalanine was treated with 300 mol percent of phenylmagnesium bromide at -78° C. and allowed to warm to room temperature. The desired ketone was not observed. Several hours of refluxing in ether and tetrahydrofuran yielded biphenyl and starting material which was optically intact.
Workup
- customwere next applied to the Grignard reaction
Sources & evidence
- ORD record
- ord-e20e9e964f654740b22c0176b22e7cf0
- Source dataset
- uspto-grants-1986_10
- Patent number
- US04618710
Reaction notes
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