5-Tert-butyl-m-xylene → 1-(Bromomethyl)-3-tert-butyl-5-methylbenzene

HRID 2396799Notes

Reaction equation

HRID 2396799 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH3:12])[CH:8]=[C:9]([CH3:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH2:12][Br:13])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 73785-Tert-butyl-m-xyleneHCID 67184N-bromobutanimide

Product 1

HCID 189846211-(Bromomethyl)-3-tert-butyl-5-methylbenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5-tert-butyl-m-xylene (15g) was dissolved in carbon tetrachloride (80ml), N-bromosuccinimide (16.45g) and a catalytic amount of azoisobutyronitrile were added and the reaction was heated at reflux for 4h. The reaction was cooled and the mixture filtered to remove the succinimide. The solvent was removed in vacuo to afford a light brown oil. Purification was carried out by chromatography on silica gel (eluting silica with 100% petroleum ether, bp 60°-800° C.) to afford 3-t-butyl-5-methylbenzyl bromide as a clear oil (15.3g). 1H NMR (360MHz, CDCl3) d 1.31 (9H; s; t-Bu), 2.34 (3H; s; CH3), 4.47 (2H; s; CH2Br), 7.04 (1H; s; Ar H), 7.13 (1H; s; Ar H), 7.25 (1H; s; Ar H). m/z (CI+)=258 (M+NH4+).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 4h
  3. temperatureThe reaction was cooled
  4. filtrationthe mixture filtered
  5. customto remove the succinimide
  6. customThe solvent was removed in vacuo
  7. customto afford a light brown oil
  8. customPurification

Sources & evidence

ORD record
ord-e06d80c5238c455daf510e9e55bff562
Source dataset
uspto-grants-1996_02
Patent number
US05494926

Reaction notes

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