四溴化碳 → 4-(Bromomethyl)-1-(4-fluorophenyl)pyrrolidin-2-one

HRID 271237笔记

反应方程式

HRID 271237 反应方程式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH2:13]O)[CH2:10][C:9]2=[O:15])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:36]>N1C=CC=CC=1>[Br:36][CH2:13][CH:11]1[CH2:12][N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:9](=[O:15])[CH2:10]1

参与物

5

反应物 3

HCID 11205四溴化碳HCID 11776三苯基膦HCID 104656771-(4-Fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one

产物 1

HCID 219354874-(Bromomethyl)-1-(4-fluorophenyl)pyrrolidin-2-one

试剂、催化剂与溶剂 1

HCID 1049吡啶溶剂

实验过程

To a cooled solution of 1-(4-fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one (0.05 g, 0.25 mmol) in pyridine (3 ml) was added triphenylphosphine (0.130 g, 0.5 mmol). The solution was stirred and carbon tetrabromide (0.08 g, 0.25 mmol) was added in 3 separate portions. The reaction mixture was then allowed to warm to room temperature and stirred for three hours. The reaction was quenched with methanol and the solvent removed. The residue was dissolved in EtOAc (75 ml) and sequentially washed with ammonium chloride (sat, 2×25 ml) and water (25 ml). The organic layer was concentrated and purified using preparative tlc (1:1 EtOac:Hexanes) to yield 4-(bromomethyl)-1-(4-fluorophenyl)pyrrolidin-2-one (HNMR).

后处理

  1. customseparate portions
  2. stirringstirred for three hours
  3. customThe reaction was quenched with methanol
  4. customthe solvent removed
  5. dissolutionThe residue was dissolved in EtOAc (75 ml)
  6. washsequentially washed with ammonium chloride (sat, 2×25 ml) and water (25 ml)
  7. concentrationThe organic layer was concentrated
  8. custompurified

来源与证据

ORD记录
ord-93f60da592cc408aa40bfb6a22ddf852
来源数据集
uspto-grants-2008_11
专利号
US07452889B2

反应笔记

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