Benzoyl Peroxide → 4-(Dibromomethyl)biphenyl

HRID 49727

Reaction equation

HRID 49727 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C1(C2C=CC(C)=CC=2)C=CC=CC=1.[Br:28]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH:2]([Br:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 125664-MethylbiphenylHCID 67184N-bromobutanimideHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-

Product 1

HCID 112442694-(Dibromomethyl)biphenyl

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-(Bromomethyl)biphenyl: A mixture of 4-phenyltoluene (4.83 g, 28.7 mmol), N-bromosuccinimide (5.64 g, 31.7 mmol), benzoyl peroxide (catalytic), and anhydrous carbon tetrachloride (35 mL) was refluxed for 24 hours. The mixture was cooled to room temperature and filtered to give a mixture (7.32 g) of 4-(dibromomethyl)biphenyl, 4-(bromomethyl)biphenyl, and 4-phenyltoluene (14:82:4 molar ratio by 1H-NMR). The product was used without further purification in the next step. 1H-NMR of the title compound (300 MHz, CDCl3) δ 7.56-7.60 (m, 4H), 7.33-7.48 (m, 5H), 4.55 (s, 2H). Partial 1H-NMR of 4-(dibromomethyl)biphenyl (300 MHz, CDCl3) δ 6.71 (s, 1H).

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-022944edb26a44fd993a171d3e1cb7fa
Source dataset
uspto-grants-2004_03
Patent number
US06706765B2

Linked notes

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