N-bromobutanimide → 1-Bromo-3-(bromomethyl)-5-methylbenzene

HRID 426179Notes

Reaction equation

HRID 426179 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([Br:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C1C(=O)N([Br:17])C(=O)C1>C(Cl)(Cl)(Cl)Cl.[W].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH2:1][Br:17])[CH:3]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 136357Benzene, 1-bromo-3,5-dimethyl-

Product 1

HCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzeneYield 72%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3,5-dimethylbromobenzene (80.25 g, 0.43M), NBS (77 g, 0.43M), and benzoyl peroxide (5.2 g, 0.021M) in carbon tetrachloride (400 ml) was refluxed for 3 hr. under a light of 500 W tungsten light. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo to give a white solid, which was purified by silica gel column chromatography (eluent, hexane) to afford 82 g (72%) of a white solid. m.p. 46-47° C.; 1H NMR (200 MHz, CDCl3) δ 2.32 (3H, s), 4.38 (2H, s), 7.12 (1H, s), 7.25 (1H, s), 7.33 (1H, s).

Workup

  1. temperaturewas refluxed for 3 hr
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customto give a white solid, which
  5. customwas purified by silica gel column chromatography (eluent, hexane)

Sources & evidence

ORD record
ord-c4a5f67c3a984322b10671c0051ad614
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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