Water → 4-Azido-3-chlorobenzyl bromide

HRID 610439ノート

反応式

HRID 610439 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 114820004-Azido-3-chlorobenzyl bromide収率 58%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4bc15961e8e341c2973c4a48ecfcfe72
出典データセット
uspto-grants-1999_12
特許番号
US05998595

反応ノート

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