Methanol → 4-Bromo-2,6-dimethylbenzamide

HRID 2427496ノート

反応式

HRID 2427496 の反応式
[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]#[N:7])=[C:4](Cl)[CH:3]=1.[OH-:12].[Na+].[CH3:14]O>>[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]([NH2:7])=[O:12])=[C:4]([CH3:14])[CH:3]=1

参加物

4

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 566042454-Bromo-2-chloro-6-methylbenzonitrile

生成物 1

HCID 544913594-Bromo-2,6-dimethylbenzamide収率 76%

実験手順

4-Bromo-2-chloro-6-methyl-benzonitrile (1.65 g, 7.16 mmol) was dissolved in methanol (20 mL) and 6M NaOH (20 mL) was added. The mixture was heated to reflux for seventeen hours. After cooling, the reaction was partitioned between diethyl ether and water. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Trituration with 10% EtOAc/Hexanes provided the title compound as a brick coloured solid (1.35 g, 76%). 1H NMR CDCl3: δ 7.41 (s, 1H), 7.29 (s, 1H), 6.33 (br s, 1H), 5.90 (br s, 1H), 2.37 (s, 3H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for seventeen hours
  3. temperatureAfter cooling
  4. customthe reaction was partitioned between diethyl ether and water
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-a4cd429cedf14183a37cb86bfbd4f936
出典データセット
uspto-grants-2011_06
特許番号
US07968570B2

反応ノート

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