Benzene → Biphenyl

HRID 2290956Notes

Reaction equation

HRID 2290956 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]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 10558934N-(Ethoxycarbonyl)alanineHCID 178418255HCID 178418255, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 7095Biphenyl

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

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

  1. 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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