2-Thiocresol → Ethyl 3-bromo-2-methoxy-(2-methylphenylthiomethyl)benzoate

HRID 2177744ノート

反応式

HRID 2177744 の反応式
[Br:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]([C:10](CSC2C=CC=CC=2)=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[SH:30].[C:31](=O)([O-])[O-].[K+].[K+]>C1COCC1>[Br:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]([CH:10]=[CH:11][C:12]=1[CH2:31][S:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH3:23])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

参加物

5

反応物 3

HCID 87122-ThiocresolHCID 11430Potassium CarbonateHCID 67107500HCID 67107500、化合物2 回

生成物 1

HCID 67107587Ethyl 3-bromo-2-methoxy-(2-methylphenylthiomethyl)benzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of ethyl 3-bromo-6-bromomethyl-2-methoxybenzoate (Intermediate 87, 0.262 g), 2-methylthiophenol (0.096 ml) and potassium carbonate (0.28 g) in THF (5 ml) was stirred at room temperature for 3 days. The resultant mixture was partitioned between ethyl acetate and NaHCO3 (saturated aqueous solution). The separated organic phase was dried (MgSO4) 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 0-30% to give ethyl 3-bromo-2-methoxy-(2-methylphenylthiomethyl)benzoate (0.24 g) as a gum.

後処理

  1. customThe resultant mixture was partitioned between ethyl acetate and NaHCO3 (saturated aqueous solution)
  2. dry with materialThe separated organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30%

出典と根拠

ORDレコード
ord-32c34a0988db45668196eeeec70cdda5
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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