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

HRID 402919ノート

反応式

HRID 402919 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-2dda80b0f9d34ab591f96ef61db502f9
出典データセット
uspto-grants-2014_06
特許番号
US08742132B2

反応ノート

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