Water → 4-Azido-3-chlorobenzyl bromide

HRID 610439노트

반응식

HRID 610439 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 114820004-Azido-3-chlorobenzyl bromide수율 58%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4bc15961e8e341c2973c4a48ecfcfe72
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998595

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