N-bromobutanimide → 2-Bromo-5-methoxybenzyl bromide

HRID 1405564Notes

Reaction equation

HRID 1405564 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH3:10].C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][Br:18]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1179151-Bromo-4-methoxy-2-methylbenzene

Product 1

HCID 35259512-Bromo-5-methoxybenzyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Into a 1000-mL round-bottom flask, was placed a solution of 1-bromo-4-methoxy-2-methylbenzene (20 g, 100.00 mmol, 1.00 equiv) in CCl4 (200 mL). Then NBS (19.58 g, 110.00 mmol, 1.10 equiv) and BPO (1.21 g, 5.00 mmol, 0.05 equiv) were added. The resulting solution was heated to reflux for 7 hs in an oil bath. The resulting solids were filtered out. The filtrate was concentrated under vacuum and applied onto a silica gel column with ethyl acetate/petroleum ether (1:500). This resulted in 5.9 g (21%) of 1-bromo-2-(bromomethyl)-4-methoxybenzene as a light yellow solid.

Workup

  1. customInto a 1000-mL round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 7 hs in an oil bath
  4. filtrationThe resulting solids were filtered out
  5. concentrationThe filtrate was concentrated under vacuum
  6. customThis resulted in 5.9 g (21%) of 1-bromo-2-(bromomethyl)-4-methoxybenzene as a light yellow solid

Sources & evidence

ORD record
ord-50b65f264e2e418ba84fe1a61cf6e0f3
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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