Water → Methyl 4-chloro-3-methoxy-5-nitrobenzoate

HRID 62754ノート

反応式

HRID 62754 の反応式
O[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:15][CH3:16].C(Cl)(=O)C([Cl:20])=O.O>CN(C=O)C>[Cl:20][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:15][CH3:16]

参加物

5

反応物 3

HCID 962WaterHCID 65578Oxalyl chlorideHCID 10878886Methyl 4-hydroxy-3-methoxy-5-nitrobenzoate

生成物 1

HCID 49757533Methyl 4-chloro-3-methoxy-5-nitrobenzoate収率 68.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A solution of methyl 4-hydroxy-3-methoxy-5-nitrobenzoate (2) (4.4 g, 19 mmol) in DMF (30 mL) at 0° C. was treated with oxalyl chloride (5.09 mL, 58.1 mmol) dropwise. The mixture was then stirred at 80° C. for 3 h under a CaCl2 drying tube. The mixture was allowed to cool to RT, poured in to iced water (100 mL) and stirred for 15 min. The precipitate was collected by filtration and washed with water and MeOH to afford methyl 4-chloro-3-methoxy-5-nitrobenzoate (3) (3.2 g, 65% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ: 8.04 (1H, d), 7.77 (1H, d), 4.04 (3H, s), 3.97 (3H, s).

後処理

  1. temperatureto cool to RT
  2. stirringstirred for 15 min
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water and MeOH

出典と根拠

ORDレコード
ord-21e65c90f3d64840828314bc29c0f638
出典データセット
uspto-grants-2016_09
特許番号
US09447028B2

反応ノート

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