Benzoyl Peroxide → HCID 117727907、化合物

HRID 1772681ノート

反応式

HRID 1772681 の反応式
[CH3:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:42])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:42][CH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2 回HCID 1074072ethyl 2-methylquinoline-4-carboxylate

生成物 1

HCID 117727907HCID 117727907、化合物

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

To a refluxing solution of ethyl 2-methylquinoline-4-carboxylate (1.6 g, 7.60 mmol) in CCl4 (150 mL), benzoyl peroxide (186 mg, 0.767 mmol) was added followed by NBS (750 g, 4.23 mmol). After 1 h, a second batch of NBS (750 g, 4.23 mmol) was added and the refluxing was continued overnight. The reaction mixture was allowed to cool to rt and washed with satd. Na2CO3. The organic layer was separated, dried (Na2SO4) and concentrated. The residue obtained was purified by flash column chromatography on silica gel (0:100-2:3 EtOAc/heptanes) to obtain ethyl 2-(bromomethyl)quinoline-4-carboxylate. Mass Spectrum (LCMS, ESI pos.) Calcd. For C13H12BrNO2: 294.0 (M+H). Found 294.1.

後処理

  1. waitthe refluxing was continued overnight
  2. washwashed with satd
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customwas purified by flash column chromatography on silica gel (0:100-2:3 EtOAc/heptanes)

出典と根拠

ORDレコード
ord-a55eabd800994591ad4ed961dcf14b64
出典データセット
uspto-grants-2016_02
特許番号
US09249163B2

反応ノート

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