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

HRID 62754노트

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HRID 62754 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 49757533Methyl 4-chloro-3-methoxy-5-nitrobenzoate수율 68.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-21e65c90f3d64840828314bc29c0f638
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447028B2

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