Methyl iodide → 1,3-Diethyl 2-(4-bromophenyl)-2-methylpropanedioate

HRID 39200노트

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HRID 39200 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:22]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:22])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10519382Diethyl 4-bromophenylmalonate

생성물 1

HCID 106163071,3-Diethyl 2-(4-bromophenyl)-2-methylpropanedioate수율 55%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of diethyl 2-(4-bromophenyl)malonate (1.5 g, 4.8 mmol) in dry THF (5 mL) at 0° C. was added sodium hydride (380 mg, 9.5 mmol). After stirring for 30 minutes at 0° C., iodomethane (600 μL, 9.5 mmol) was added and the reaction was allowed to warm to room temperature. After stirring for 12 h at room temperature, the reaction was quenched with water (3 mL). The mixture was partitioned between 1 N HCl (10 mL) and dichloromethane (10 mL), and the organic layer was separated. The organic layer was washed with 1 N HCl (10 mL), dried over Na2SO4 and evaporated. The crude material was purified by silica gel chromatography, eluting with 0-20% ethyl acetate in hexanes, to give diethyl 2-(4-bromophenyl)-2-methylmalonate (850 mg, 55%) 1H NMR (400 MHz, DMSO-d6) δ 7.59-7.55 (m, 2H), 7.31-7.27 (m, 2H), 4.21-4.14 (m, 4H), 1.75 (s, 3H), 1.19-1.16 (m, 6H).

후처리

  1. temperatureto warm to room temperature
  2. stirringAfter stirring for 12 h at room temperature
  3. customthe reaction was quenched with water (3 mL)
  4. customThe mixture was partitioned between 1 N HCl (10 mL) and dichloromethane (10 mL)
  5. customthe organic layer was separated
  6. washThe organic layer was washed with 1 N HCl (10 mL)
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. customThe crude material was purified by silica gel chromatography
  10. washeluting with 0-20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-16879a0a0bc44b89958b8465a906fb28
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524767B2

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