N-bromobutanimide → 1-Azido-4-(bromomethyl)benzene

HRID 429156

Reaction equation

HRID 429156 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[Br:11]N1C(=O)CCC1=O>C1C=CC=CC=1>[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:11])=[CH:6][CH:5]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1374301-Azido-4-methylbenzene

Product 1

HCID 118166671-Azido-4-(bromomethyl)benzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To p-azidotoluene (2.2 mM) prepared as above was added N-bromosuccinimide (2.48 mM), and azo-isobutyronitrile (0.214 mM) in anhydrous benzene (5 ml). This was left to reflux for 5 hours, with the reaction being monitored by TLC. The organics were extracted into diethyl ether (3×15 ml), and water, dried over magnesium sulphate, and the excess solvent removed under vacuum. The p-azidobenzyl bromide formed was isolated using chromatographic techniques.

Workup

  1. waitThis was left
  2. temperatureto reflux for 5 hours, with the reaction
  3. extractionThe organics were extracted into diethyl ether (3×15 ml), and water
  4. dry with materialdried over magnesium sulphate
  5. customthe excess solvent removed under vacuum

Sources & evidence

ORD record
ord-bcba20d3fe4b41b1b42ec62cfc230ac1
Source dataset
uspto-grants-2001_11
Patent number
US06316455B1

Linked notes

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