溴离子(溴化物)标准溶液 → Ethyl 4-(4-(4-Chloro-2-fluorophenoxy)phenoxy)pentanoate

HRID 4460

反应方程式

HRID 4460 反应方程式
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[C:4]([F:16])[CH:3]=1.Br[CH:18]([CH3:26])[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+].[Br-].C(=O)([O-])[O-].C1(O)C=CC=CC=1.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([O:13][CH:18]([CH3:26])[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:11][CH:12]=2)=[C:4]([F:16])[CH:3]=1

参与物

9

反应物 7

HCID 259溴离子(溴化物)标准溶液HCID 313海萝胶HCID 996苯酚HCID 11430碳酸钾HCID 19660Carbonate IonHCID 316888乙基 4-溴戊酯HCID 140726804-(4-Chloro-2-fluorophenoxy)phenol

产物 1

HCID 13880907Ethyl 4-(4-(4-Chloro-2-fluorophenoxy)phenoxy)pentanoate

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
130 °C

实验过程

A stirred mixture of 4-(4-chloro-2-fluorophenoxy)phenol (2.3 g, 0.0103 mol), ethyl 4-bromopentanoate (2.01 g, 0.0103 mol), and potassium carbonate (1.46 g, 0.105 mol) in DMF (20 ml) was heated in an oil bath at 130° C. for one hour. Additional bromide (0.5 g) and carbonate (0.5 g) were added each hour for the next four hours. At the end of this period, gas chromatography indicated that most of the starting phenol had reacted. After cooling, the reaction mixture was poured into 4N HCl solution (200 ml), and the product extracted into a 1:1 mixture of ether-pentane (2×150 ml). The organic extracts were combined, washed with 10% NaOH solution (200 ml), dried (MgSO4), then the solvent evaporated. The resulting orange oil was purified via preparative HPLC (9:1 hexane/ethyl acetate) with the second peak being collected. Removal of the solvent gave the desired ester as a light yellow oil: RI=1.5344 @ 25° C. Calc: C, 62.21; H, 5.50. Found: C, 62.38; H, 5.33.

后处理

  1. customhad reacted
  2. temperatureAfter cooling
  3. extractionthe product extracted into a 1:1 mixture of ether-pentane (2×150 ml)
  4. washwashed with 10% NaOH solution (200 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated
  7. customThe resulting orange oil was purified via preparative HPLC (9:1 hexane/ethyl acetate) with the second peak
  8. custombeing collected
  9. customRemoval of the solvent

来源与证据

ORD记录
ord-53fcb22988bf4f00ace4b323695f617b
来源数据集
uspto-grants-1988_02
专利号
US04725683

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