N-bromobutanimide → 3-Methoxy-4-nitrobenzyl bromide

HRID 2258541Notes

Reaction equation

HRID 2258541 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:12])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH2:12][C:5]1[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 974555-Methyl-2-nitroanisole

Product 1

HCID 126216043-Methoxy-4-nitrobenzyl bromideYield 38.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 20 g of 3-methoxy-4-nitrotoluene, 21.6 g of N-bromosuccinimide and 0.3 g of dibenzoyl peroxide in 120 ml of CCl4 is heated at reflux for 5 hours. The solvent is evaporated off under vacuum, the residue is taken up in water, extracted with DCM, washed with water, dried over Na2SO4 and evaporated under vacuum. 11.35 g of the expected product are obtained after crystallization from EtOH, mp=98° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent is evaporated off under vacuum
  4. extractionextracted with DCM
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-bd69583dd8fd4811b629cf67e43ea5ba
Source dataset
uspto-grants-1997_08
Patent number
US05661169

Reaction notes

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