Water → 4-Azido-3-chlorobenzyl bromide

HRID 610439Notes

Reaction equation

HRID 610439 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[Cl:11])=[N+:2]=[N-:3].[Br:12]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.O>C1C=CC=CC=1>[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:12])=[CH:6][C:5]=1[Cl:11])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 154333821-Azido-2-chloro-4-methylbenzene

Product 1

HCID 114820004-Azido-3-chlorobenzyl bromideYield 58%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Azido-3-chlorotoluene (17.14 g, 0.1 mol) was dissolved in dry benzene (80 ml) and thereto were added N-bromosuccinimide (19.6 g, 0.11 mol) and AIBN (1.64 g, 0.01 mol). The resulting mixture was refluxed in the shade in a nitrogen stream for 10 hr. Water (100 ml) was added and the mixture was filtrated. The aqueous layer of the filtrate was taken and extracted with ether. The organic layers were combined, washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained brown oil was purified by silica gel column chromatography (eluent; hexane) to give the title compound (14.2 g, yield 58%). m.p.: 75-77° C.

Workup

  1. temperatureThe resulting mixture was refluxed in the shade in a nitrogen stream for 10 hr
  2. filtrationthe mixture was filtrated
  3. extractionextracted with ether
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained brown oil was purified by silica gel column chromatography (eluent; hexane)

Sources & evidence

ORD record
ord-4bc15961e8e341c2973c4a48ecfcfe72
Source dataset
uspto-grants-1999_12
Patent number
US05998595

Reaction notes

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