Benzene → 3-Chlorobiphenyl

HRID 905329Notes

Reaction equation

HRID 905329 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)N.N(OC(C)(C)C)=O.[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[Cu]>[Cl:1][C:2]1[CH:3]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 79323-ChloroanilineHCID 10906Tert-Butyl nitrite

Product 1

HCID 163223-ChlorobiphenylYield 67.6%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

In a manner similar to Example 1, the reaction of 3-chloroaniline (38.3 g, 0.30 mole) with t-butyl nitrite (46.4 g, 0.45 mole) in the presence of copper powder (15.0 g, 0.24 mole) and 4Å molecular sieves (powdered, 15.0 g) in benzene (1650 ml) produced 3-chloro[1,1'-biphenyl] (38.4 g, 67.6% yield, bp 96°/0.15 mm) as an oil. When the experiment was repeated the yield was 65.7%

Sources & evidence

ORD record
ord-6a1a366cf55c4837bb35d83c4d83a7a9
Source dataset
uspto-grants-1983_12
Patent number
US04423234

Reaction notes

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