苯硫酚 → 2-(3,5-Dimethoxyphenyl)-2-(phenylsulfanyl)acetic acid

HRID 1666307

反应方程式

HRID 1666307 反应方程式
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:20](Br)[C:21]([O:23]C)=[O:22])[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1>O1CCOCC1>[CH3:19][O:18][C:16]1[CH:15]=[C:14]([CH:20]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:21]([OH:23])=[O:22])[CH:13]=[C:12]([O:11][CH3:10])[CH:17]=1

参与物

5

反应物 3

HCID 7969苯硫酚HCID 14797氢氧化钾2 次HCID 19010509Methyl 2-(3,5-dimethoxyphenyl)-2-bromoacetate

产物 1

HCID 670817982-(3,5-Dimethoxyphenyl)-2-(phenylsulfanyl)acetic acid

试剂、催化剂与溶剂 1

HCID 312751,4-二氧六环溶剂2 次

反应条件

温度
80 °C

实验过程

A mixture of benzenethiol (5.91 g) and potassium hydroxide (3.48 g) in dioxane (200 ml) was heated at 80° C. for one hour under nitrogen. After cooling down to 20° C., a solution of methyl 2-(3,5-dimethoxyphenyl)-2-bromoacetate (15.0 g) in dioxane (100 ml) was added and the mixture was refluxed for two hours. Additionally potassium hydroxide (1.5 g) was added and the reflux continued for further two hours. After cooling to room temperature, the suspension was filtered and the filtrate concentrated to dryness. The residue was partitioned between dichloromethane (300 ml) and aqueous hydrochloric acid (1M, 300 ml). The organic phase was dried and concentrated to dryness, leaving crude 2-(3,5-dimethoxyphenyl)-2-(phenylsulfanyl)acetic acid. Crystallization from diethyl ether gave the pure compound (7.2 g), m.p. 124-126° C.

后处理

  1. temperatureAfter cooling down to 20° C.
  2. temperaturethe mixture was refluxed for two hours
  3. temperatureAfter cooling to room temperature
  4. filtrationthe suspension was filtered
  5. concentrationthe filtrate concentrated to dryness
  6. customThe residue was partitioned between dichloromethane (300 ml) and aqueous hydrochloric acid (1M, 300 ml)
  7. customThe organic phase was dried
  8. concentrationconcentrated to dryness

来源与证据

ORD记录
ord-c0f83d0188c544b68f7c740523548e2f
来源数据集
uspto-grants-2011_10
专利号
US08044067B2

关联笔记

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