Diethyl methylmalonate → Diethyl 2-(2-bromo-4-nitrophenyl)-2-methylmalonate

HRID 39191

반응식

HRID 39191 반응식
[CH3:1][CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[Br:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1F>CN(C=O)C>[Br:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[C:2]([CH3:1])([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

참가 물질

5

반응물 3

HCID 11857Diethyl methylmalonateHCID 24758Sodium hydrideHCID 696992-Bromo-1-fluoro-4-nitrobenzene

생성물 1

HCID 59206132Diethyl 2-(2-bromo-4-nitrophenyl)-2-methylmalonate수율 99%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

Diethyl 2-methylmalonate (4.31 mL, 25.0 mmol) was dissolved in 25 mL of anhydrous DMF. This solution was cooled to 0° C. under an atmosphere of nitrogen. Sodium hydride (1.04 g, 26 mmol, 60% by weight in mineral oil) was slowly added to the solution. The resulting mixture was allowed to stir for 3 minutes at 0° C., and then at room temperature for 10 minutes. 2-Bromo-1-fluoro-4-nitrobenzene (5.00 g, 22.7 mmol) was quickly added and the mixture turned bright red. After stirring for 10 minutes at room temperature, the crude mixture was evaporated to dryness and then partitioned between dichloromethane and a saturated aqueous solution of sodium chloride. The layers were separated and the organic phase was washed twice with a saturated aqueous solution of sodium chloride. The organics were concentrated to yield diethyl 2-(2-bromo-4-nitrophenyl)-2-methylmalonate (8.4 g, 99%) as a pale yellow oil which was used without further purification. Retention time 1.86 min.

후처리

  1. waitat room temperature for 10 minutes
  2. stirringAfter stirring for 10 minutes at room temperature
  3. customthe crude mixture was evaporated to dryness
  4. custompartitioned between dichloromethane
  5. customThe layers were separated
  6. washthe organic phase was washed twice with a saturated aqueous solution of sodium chloride
  7. concentrationThe organics were concentrated

출처 및 근거

ORD 기록
ord-36d28dae0c694402b63d442f4eef0be0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524767B2

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