8-Methylquinoline → 8-(Bromomethyl)quinoline

HRID 911344

반응식

HRID 911344 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C1C(=O)N([Br:19])C(=O)C1>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

참가 물질

5

반응물 2

HCID 119108-MethylquinolineHCID 67184N-bromobutanimide

생성물 1

HCID 3469148-(Bromomethyl)quinoline수율 83.7%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

Combine 8-methyl-quinoline (1.0 g, 6.99 mmol), NBS (1.3 g, 7.13 mmol), benzoyl peroxide (6.0 mg, 0.03 mmol), carbon tetrachloride (30 mL) and reflux for 17 h. Cool the reaction mixture to ambient temperature and evaporate the solvent. Dissolve the residue in chloroform (30 mL), wash the organic solution with saturated aqueous NaHCO3 (2×10 mL), brine (10 mL) and dry over anhydrous Na2SO4. Evaporate the solvent and purify by chromatography on silica gel eluting with DCM to obtain the title compound as a white solid (1.3 g, 83%). MS (ES+) m/z: 223 (M+H)+.

후처리

  1. customevaporate the solvent
  2. dissolutionDissolve the residue in chloroform (30 mL)
  3. washwash the organic solution with saturated aqueous NaHCO3 (2×10 mL), brine (10 mL)
  4. dry with materialdry over anhydrous Na2SO4
  5. customEvaporate the solvent
  6. custompurify by chromatography on silica gel eluting with DCM

출처 및 근거

ORD 기록
ord-5f78717363864841a89c26a5b8c91846
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

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