4-溴茴香硫醚 → Dimethyl 2-thioanisylterepthalate

HRID 1885379

反应方程式

HRID 1885379 反应方程式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.[Li][C:11](C)(C)C.[CH3:15][O:16][C:17](=[O:29])[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=1Br>O1CCCC1.[Cl-].[Cl-].[Zn+2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Cl-].[Ni+2]>[CH3:11][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][C:3]=1[C:19]1[CH:20]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[CH:26]=[CH:27][C:18]=1[C:17]([O:16][CH3:15])=[O:29]

参与物

7

反应物 3

HCID 660374-溴茴香硫醚HCID 87741邻溴对二苯甲酸二甲酯HCID 178418306HCID 178418306，化合物

产物 1

HCID 86744855Dimethyl 2-thioanisylterepthalate

试剂、催化剂与溶剂 3

HCID 84306Bis(triphenylphosphine)nickel(II)chloride催化剂HCID 3007855氯化锌催化剂HCID 8028四氢呋喃溶剂2 次

实验过程

4-Bromothioanisole (7.1 g) was dissolved in tetrahydrofuran (23 ml). To this solution at -78° C. under nitrogen was added over a ten minute period 1.7M tBuLi (48 ml). After 45 minutes at room temperature, 1M ZnCl2 (41 ml) was added dropwise over a ten minute period. After one half hour at room temperature, bis(triphenylphosphine)nickel (II) chloride (1.4 g) was added followed by dimethyl-2-bromoterepthalate (4.67 g) in tetrahydrofuran (47 ml). The reaction mixture was stirred at room temperature for 45 minutes. The THF was removed under reduced pressure. The residue was treated with ethyl acetate and 1N HCl and the layers separated. The organic phase was washed with water, brine, dried over magnesium sulfate and evaporated gave the crude product. Chromatography on silica gel using 15% ethyl acetate/hexanes gave the desired product (3.92 g).

后处理

  1. waitAfter one half hour at room temperature
  2. customThe THF was removed under reduced pressure
  3. additionThe residue was treated with ethyl acetate and 1N HCl
  4. customthe layers separated
  5. washThe organic phase was washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customgave the crude product

来源与证据

ORD记录
ord-7b007aac96c4449dbda050f0741bda68
来源数据集
uspto-grants-1992_09
专利号
US05144028

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