N-bromobutanimide → 3-(Bromomethyl)-3'-chloro-1,1'-biphenyl

HRID 485535Notes

Reaction equation

HRID 485535 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:14][C:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27576743-Chloro-3'-methyl-1,1'-biphenyl

Product 1

HCID 155886493-(Bromomethyl)-3'-chloro-1,1'-biphenylYield 93.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3'-Chloro-3-methyl[1,1'-biphenyl] (7.0 g, 0.035 mole) and N-bromosuccinimide (6.4 g, 0.035 mole) in 100 ml of carbon tetrachloride were irradiated for 4 hours with white light to afford 3-bromomethyl-3'-chloro[1,1'-biphenyl] (9.2 g). The nmr spectrum was consistent with that expected for the named compound.

Sources & evidence

ORD record
ord-93adf30706224380833f88fb15bca0f4
Source dataset
uspto-grants-1985_08
Patent number
US04536591

Reaction notes

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