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

HRID 2177749ノート

反応式

HRID 2177749 の反応式
[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]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 23642ThioguaiacolHCID 67107930Methyl 3-bromo-6-bromomethyl-2-hydroxybenzoate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-ea88bd49a3124918876501837993a031
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

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