Potassium Carbonate → Ethyl 3-(2-hydroxy-2-methylpropoxy)-4-bromobenzoate

HRID 2102893ノート

反応式

HRID 2102893 の反応式
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[OH:13].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22]([CH3:25])([OH:24])[CH3:23]>CN(C=O)C>[OH:24][C:22]([CH3:25])([CH3:23])[CH2:21][O:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[Br:1])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 684091-Chloro-2-methylpropan-2-olHCID 12134897Ethyl 4-bromo-3-hydroxybenzoate

生成物 1

HCID 57804223Ethyl 3-(2-hydroxy-2-methylpropoxy)-4-bromobenzoate収率 26%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Ethyl 4-bromo-3-hydroxybenzoate (1.5 g, 6.12 mmol), potassium carbonate (5.07 g, 36.72 mmol) and 1-chloro-2-methylpropan-2-ol (0.75 mL, 7.34 mmol) were placed in 50 mL DMF and the reaction was heated at 80° C. for 18 h. The mixture was cooled and partitioned between EtOAc and water. The organic layer was separated, washed with water, brine, dried (Na2SO4), filtered, and the filtrate was concentrated under vacuum to an oil. Purification by column chromatography on silica gel using EtOAc/hexane (0-50%) gave the product (0.5 g, 26%) as a yellow oil.

後処理

  1. temperatureThe mixture was cooled
  2. custompartitioned between EtOAc and water
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under vacuum to an oil
  8. customPurification by column chromatography on silica gel

出典と根拠

ORDレコード
ord-5398f02845a54f9caff94ec8944468e3
出典データセット
uspto-grants-2009_08
特許番号
US07576099B2

反応ノート

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