N-bromobutanimide → 2-Azido-1-(bromomethyl)-4-iodobenzene

HRID 1869753Notes

Reaction equation

HRID 1869753 reaction equation
[N:1]([C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[CH3:11])=[N+:2]=[N-:3].[Br:12]N1C(=O)CCC1=O>C1C=CC=CC=1>[N:1]([C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[CH2:11][Br:12])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 579875492-Azido-4-iodo-1-methylbenzene

Product 1

HCID 579873052-Azido-1-(bromomethyl)-4-iodobenzeneYield 67.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of the azide from step 1 (9.1 g, 0.035M), N-Bromosuccinimide (6.8 g, 0.039M) and 1,1azobis(cyclohexanecarbonitrile) (0.85 g, 3.5 mmol) in benzene (40 ml) was heated at reflux overnight. The solvent was evaporated under vacuum and the residue was diluted EtOAc (100 ml) and washed with water (50 ml) and brine, dried (MgSO4) and concentrated under vacuum. The residue was purified by chromatography (silica, hexanes) to give the azide as a white solid (8 g, 67%). 1H NMR (500 MHz, CDCl3): δ 4.30 (2H, s), 6.98 (1H, d, J 8.0), 7.35 (2H, t, J 7.0).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated under vacuum
  4. washwashed with water (50 ml) and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by chromatography (silica, hexanes)

Sources & evidence

ORD record
ord-2712c556c46f4892a5de18991fb307c6
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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