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

HRID 1643352Notes

Reaction equation

HRID 1643352 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.CCCCCC.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 94.2%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolventHCID 8058HexaneSolvent

Procedure

A mixture of 3,5-dimethylbromobenzene (70 g, 0.378 M), NBS (67.3 g, 0.373 M), and benzoyl peroxide (2.27 g, 0.009 M) in carbon tetrachloride (300 mL) was refluxed for 3 hr. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo to give a pale brown oil. The crude product was dissolved in hexane and filtered through a short silica gel pad (diameter: 9.5 cm, height: 7 cm). The silica gel pad was washed with hexane until the product eluted completely. The filtrate was evaporated in vacuo to give 94 g of 1-bromo-3-(bromomethyl)-5-methylbenzene (contaminated with starting material and 1-bromo-3,5-bis-bromomethylbenzene) as a pale brown oil, which solidified on standing at room temperature. The mixture was used directly in the next reaction without further purification.

Workup

  1. temperaturewas refluxed for 3 hr
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customto give a pale brown oil
  5. filtrationfiltered through a short silica gel pad (diameter: 9.5 cm, height: 7 cm)
  6. washThe silica gel pad was washed with hexane until the product
  7. washeluted completely
  8. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-d89c5f57c1684aa5b7c64b5fc0d5f365
Source dataset
uspto-grants-2012_02
Patent number
US08119800B2

Reaction notes

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