N-bromobutanimide → 2-Bromo-4-(bromomethyl)-1-methoxybenzene

HRID 491412Notes

Reaction equation

HRID 491412 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Br:11]N1C(=O)CCC1=O>CC(N=NC(C#N)(C)C)(C#N)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:9][CH3:10])[CH2:8][Br:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 891432-Bromo-4-methylanisole

Product 1

HCID 112774622-Bromo-4-(bromomethyl)-1-methoxybenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 6547AzobisisobutyronitrileCatalyst

Procedure

2-Bromo-4-methyl anisole 14 (2.2 mL, 14.9 mmol) was dissolved in dichlomethane (30 mL) and N-bromosuccinimide (3.75 g, 16.4 mmol) was added followed by AIBN (26.0 mg). The reaction was heated to reflux for 19 hrs., then cooled to room temperature and the precipitate was filtered off. The filtrate was diluted with dichloromethane and washed with 0.5 M aqueous sodium bicarbonate, followed by water. The organic mixture was dried over sodium sulfate, filtered and concentrated under vacuum to yield 15 (4.16 g, 100%). The benzyl bromide was used as the crude material without further purification.

Workup

  1. additionwas added
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 19 hrs
  4. filtrationthe precipitate was filtered off
  5. additionThe filtrate was diluted with dichloromethane
  6. washwashed with 0.5 M aqueous sodium bicarbonate
  7. dry with materialThe organic mixture was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5109376a568e483292ffa4820f2aa5f8
Source dataset
uspto-grants-2009_05
Patent number
US07531544B2

Reaction notes

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