海萝胶 → 4-环丙基苯硼酸

HRID 19829

反应方程式

HRID 19829 反应方程式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[B:11](OC(C)C)([O:16]C(C)C)[O:12]C(C)C.Cl>CCCCCC.C1COCC1.C1(C)C=CC=CC=1>[CH:8]1([C:5]2[CH:6]=[CH:7][C:2]([B:11]([OH:16])[OH:12])=[CH:3][CH:4]=2)[CH2:10][CH2:9]1

参与物

7

反应物 3

HCID 313海萝胶HCID 21531硼酸三异丙酯HCID 122213551-Bromo-4-cyclopropylbenzene

产物 1

HCID 28494284-环丙基苯硼酸

试剂、催化剂与溶剂 3

HCID 1140甲苯溶剂HCID 8028四氢呋喃溶剂HCID 8058正己烷溶剂

反应条件

温度
-70 °C

实验过程

2.5 M nButyllithium in hexane (14.5 mL) is added dropwise to 1-bromo-4-cyclopropyl-benzene (5.92 g) in THF (14 mL) and toluene (50 mL) chilled to −70° C. The resultant solution is stirred at −70° C. for 30 min before triisopropyl borate (8.5 mL) is added. The solution is warmed to −20° C. and then treated with 4 M aqueous hydrochloric acid (15.5 mL). The reaction mixture is further warmed to room temperature and then the organic phase is separated. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (sodium sulphate). The solvent is evaporated and the residue is washed with a mixture of ether and cyclohexane to give the product as a colorless solid.

后处理

  1. additionis added
  2. temperatureThe solution is warmed to −20° C.
  3. temperatureThe reaction mixture is further warmed to room temperature
  4. customthe organic phase is separated
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. dry with materialthe combined organic phases are dried (sodium sulphate)
  7. customThe solvent is evaporated
  8. washthe residue is washed with a mixture of ether and cyclohexane

来源与证据

ORD记录
ord-0ba6ce0f6e0e40739ff825ced6ba4d1c
来源数据集
uspto-grants-2010_06
专利号
US07745414B2

关联笔记

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