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

HRID 2102893노트

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HRID 2102893 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5398f02845a54f9caff94ec8944468e3
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576099B2

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