1,2-二氯乙烷 → (4-Bromo-3-fluorophenyl)(morpholin-4-yl)methanone

HRID 882965

反应方程式

HRID 882965 反应方程式
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N1CCOCC1)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:8])=[CH:4][C:3]=1[F:11]

参与物

7

反应物 5

HCID 111,2-二氯乙烷HCID 7525N-乙基吗啉HCID 80831,4-氧氮六环HCID 757711-羟基苯并三唑(HOBT)HCID 27733414-溴-3-氟苯甲酸

产物 1

HCID 48474115(4-Bromo-3-fluorophenyl)(morpholin-4-yl)methanone收率 98.5%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

A 500 mL flask was charged with 4-bromo-3-fluorobenzoic acid (5.00 g, 22.83 mmol), 100 mL DMF, morpholine (2.4 ml, 27.5 mmol), and 4-Ethylmorpholine (8.6 ml, 67.9 mmol). HOBt (4.32 g, 32.0 mmol) was added followed by EDC (5.25 g, 27.4 mmol) and the reaction allowed to stir at room temperature for 18 hours. The reaction was concentrated and the resulting orange syrup taken up in 100 mL EtOAc and 100 mL water. The organic layer was washed with 100 mL 2N HCl, 100 mL saturated sodium bicarbonate, and 100 mL saturated sodium chloride. The organic was then dried with MgSO4, filtered, and concentrated to give 6.476 g (98%) of a viscous yellow oil. This material was used without further purification.

后处理

  1. concentrationThe reaction was concentrated
  2. washThe organic layer was washed with 100 mL 2N HCl, 100 mL saturated sodium bicarbonate, and 100 mL saturated sodium chloride
  3. dry with materialThe organic was then dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

来源与证据

ORD记录
ord-77d51c2daee940da81507bf578f69cff
来源数据集
uspto-grants-2012_08
专利号
US08236799B2

关联笔记

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