Potassium Carbonate → 5-Bromo-2-(1-ethoxycarbonyl-ethoxy)-benzoic acid methyl ester

HRID 402919노트

반응식

HRID 402919 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[OH:11].[CH2:13]([O:15][C:16](=[O:20])[CH:17](Br)[CH3:18])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[O:11][CH:17]([C:16]([O:15][CH2:13][CH3:14])=[O:20])[CH3:18]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 77683Methyl 5-bromosalicylateHCID 79040Ethyl 2-bromopropionate

생성물 1

HCID 591920375-Bromo-2-(1-ethoxycarbonyl-ethoxy)-benzoic acid methyl ester수율 100%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of 5-bromo-2-hydroxy-benzoic acid methyl ester (25.0 g, 103 mmol), 2-bromo-propionic acid ethyl ester (18.6 g, 103 mmol) and potassium carbonate (50.2 g, 360 mmol) in acetone (500 mL) is heated under reflux for 24 h. The reaction mixture is filtered, and the filtrate concentrated by rotary evaporation. The residue is dissolved in dichloromethane and washed twice with water. The organic layer is dried over Na2SO4, filtered and concentrated at reduced pressure to afford the title compound as a colorless oil (34.1 g, 103 mmol, 100%). 1H NMR (400 MHz, CDCl3, 298 K): δ=7.91 (d, J=2.7 Hz, 1H), 7.49 (dd, J=8.8, 2.7 Hz, 1H), 6.75 (d, J=8.8 Hz, 1H), 4.71 (q, J=6.8 Hz, 1H), 4.20 (q, J=7.1 Hz, 2H), 3.88 (s, 3H), 1.65 (d, J=6.8 Hz, 3H), 1.23 (t, J=7.1 Hz, 3H). MS (ES+): 331 (M(C13H1579BrO5)+H)+.

후처리

  1. temperatureis heated
  2. temperatureunder reflux for 24 h
  3. filtrationThe reaction mixture is filtered
  4. concentrationthe filtrate concentrated by rotary evaporation
  5. dissolutionThe residue is dissolved in dichloromethane
  6. washwashed twice with water
  7. dry with materialThe organic layer is dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated at reduced pressure

출처 및 근거

ORD 기록
ord-2dda80b0f9d34ab591f96ef61db502f9
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742132B2

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