8-Methylquinoline → 8-(Bromomethyl)quinoline

HRID 911344

反応式

HRID 911344 の反応式
[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

参加物

5

反応物 2

HCID 119108-MethylquinolineHCID 67184N-bromobutanimide

生成物 1

HCID 3469148-(Bromomethyl)quinoline収率 83.7%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-5f78717363864841a89c26a5b8c91846
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

関連ノート

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