Benzoyl Peroxide → 2-Bromo-1-(bromomethyl)-4-tert-butylbenzene

HRID 557501Notes

Reaction equation

HRID 557501 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[CH3:12].[Br:13]Br.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[H][H]>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[CH2:12][Br:13]

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 24408Bromine2×HCID 3200772-bromo-4-tert-butyl-1-methylbenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 453576952-Bromo-1-(bromomethyl)-4-tert-butylbenzeneYield 89.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideCatalyst

Procedure

To a mixture of 227 g (1.00 mol) of 2-bromo-4-tert-butyl-1-methylbenzene, 160 g (1.00 mol) of bromine and 1.4 liter of CCl4 1.0 g of benzoyl peroxide was added. This mixture was refluxed until evolution of hydrogen bomide was stopped, and red color of bromine disappeared. The resulting mixture was evaporated using rotary evaporated. Fractional rectification of the residue gave 273 g (89%) of the title product, b.p. 138° C.-141° C./4 mm Hg. Anal. calc. for C11H14Br2: C, 43.17; H, 4.61. Found: C, 43.30; H, 6.72. 1H NMR (CDCl3): δ 7.56 (d, J=1.8 Hz, 3-H), 7.37 (d, J=8.1 Hz, 1H, 5-H), 7.30 (dd, J=8.1 Hz, J=1.8 Hz, 1H, 6-H), 4.59 (s, 2H, CH2Br), 1.29 (s, 9H, tBu). 13C{1H} NMR (CDCl3): δ 153.9, 133.9, 130.9, 130.4, 125.1, 124.4, 34.7, 33.4, 31.06.

Workup

  1. additionwas added
  2. customThe resulting mixture was evaporated

Sources & evidence

ORD record
ord-23ad077974704391a8d21443e8162e32
Source dataset
uspto-grants-2011_11
Patent number
US08058461B2

Reaction notes

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