Benzoyl Peroxide → 1,3-Dibromo-2-(bromomethyl)-5-methoxybenzene

HRID 394051Notes

Reaction equation

HRID 394051 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Br:10])[C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Br:10])[C:3]=1[CH2:11][Br:12]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 845133,5-Dibromo-4-methylanisole

Product 1

HCID 34078661,3-Dibromo-2-(bromomethyl)-5-methoxybenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a suspension of 5.0 g of 2,6-dibromo-4-methoxytoluene in 90 mL of CCl4 was added N-bromosuccinimide and benzoyl peroxide. The resulting mixture was heated to reflux and stirred at the refluxing temperature while irradiating with a sunlamp for 2 h, then cooled and concentrated. The resulting residue was dissolved in 1:1 hexanes-Et2O and filtered through a pad of silica gel, then purified by flash chromatography on a Biotage 40M column, eluting with 98:2 hexanes-Et2O, to yield 2,6-Dibromo-4-methoxy-benzyl bromide as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 7.11 (s, 2H); 4.82 (s, 2H); 3.80 (s, 3H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. customwhile irradiating with a sunlamp for 2 h
  4. temperaturecooled
  5. concentrationconcentrated
  6. dissolutionThe resulting residue was dissolved in 1:1 hexanes-Et2O
  7. filtrationfiltered through a pad of silica gel
  8. custompurified by flash chromatography on a Biotage 40M column
  9. washeluting with 98:2 hexanes-Et2O

Sources & evidence

ORD record
ord-5b33f7bb13d140bdb66523e4a8732f8f
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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