Azobisisobutyronitrile → 1-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}naphthalene

HRID 1875047ノート

反応式

HRID 1875047 の反応式
[Cl:1][C:2]1[C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)=[C:6]([F:19])[C:5]([CH3:20])=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:20][C:5]1[C:6]([F:19])=[C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[C:2]([Cl:1])=[CH:3][CH:4]=1

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 684882771-[(6-Chloro-2-fluoro-3-methylphenyl)oxy]naphthalene

生成物 1

HCID 684855581-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}naphthalene収率 45.5%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

To a solution of 1-[(6-chloro-2-fluoro-3-methylphenyl)oxy]naphthalene (1.69 g, 5.89 mmol) in carbon tetrachloride (20 mL) was added N-bromosuccinimide (1.154 g, 6.48 mmol) and AIBN (0.048 g, 0.295 mmol). The mixture was heated at reflux overnight. The reaction mixture was filtered through Celite and the solvent was evaporated. The residue was purified by flash chromatography (hexane:ethyl acetate) to give the desired product (0.98 g, 45.5%) as a light yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 8.43-8.51 (m, 1H), 7.84-7.92 (m, 1H), 7.53-7.64 (m, 3H), 7.23-7.34 (m, 3H), 6.50 (d, 1H), 4.50 (d, 2H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered through Celite
  4. customthe solvent was evaporated
  5. customThe residue was purified by flash chromatography (hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-aedcfd401bbe4b488797dda86d99bc54
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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