Potassium Carbonate → Methyl 3-bromo-2-hydroxy-6-(2-methoxyphenylthiomethyl)benzoate

HRID 2177749노트

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HRID 2177749 반응식
[Br:1][C:2]1[C:3]([OH:14])=[C:4]([C:9]([CH2:12]Br)=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[SH:23].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Br:1][C:2]1[C:3]([OH:14])=[C:4]([C:9]([CH2:12][S:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH3:15])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 23642ThioguaiacolHCID 67107930Methyl 3-bromo-6-bromomethyl-2-hydroxybenzoate2회

생성물 1

HCID 67107461Methyl 3-bromo-2-hydroxy-6-(2-methoxyphenylthiomethyl)benzoate수율 64.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

A mixture of methyl 3-bromo-6-bromomethyl-2-hydroxybenzoate (Intermediate 53, 0.6 g), 2-methoxythiophenol (0.518 g) and potassium carbonate (0.766 g) in THF (10 ml) was stirred and heated at 60° C. for 3 hours. After cooling, the mixture was partitioned between ethyl acetate and water and the separated organic layer was washed with potassium hydroxide solution, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-15% to give methyl 3-bromo-2-hydroxy-6-(2-methoxyphenylthiomethyl)-benzoate (0.46 g) as a white solid which was used without further characterisation.

후처리

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between ethyl acetate and water
  3. washthe separated organic layer was washed with potassium hydroxide solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-15%

출처 및 근거

ORD 기록
ord-ea88bd49a3124918876501837993a031
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067905B2

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