Water → Methyl 2-(2-bromophenyl)-5-chloropentanoate

HRID 1009454노트

반응식

HRID 1009454 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[H-].[Na+].[Cl:15][CH2:16][CH2:17][CH2:18]I.O>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH2:18][CH2:17][CH2:16][Cl:15])[C:9]([O:11][CH3:12])=[O:10]

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 8063364Methyl 2-(2-bromophenyl)acetate

생성물 1

HCID 67067456Methyl 2-(2-bromophenyl)-5-chloropentanoate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매3회HCID 8857Ethyl Acetate용매

실험 절차

A solution of methyl 2-bromophenylacetate (2.0 g) in DMF (5 mL) was added to a suspension of sodium hydride (containing mineral oil at 40%, 384 mg) in DMF (20 mL) under ice-cooling. The reaction solution was stirred for 10 minutes, further stirred at room temperature for 30 minutes and then ice-cooled again. A solution of 1-chloro-3-iodopropane (1.96 g) in DMF (5 mL) was added to the reaction mixture, and the reaction solution was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. The resulting organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain a crude product of methyl 2-(2-bromophenyl)-5-chloropentanoate. Hydrazine monohydrate (4 mL) was added to a solution of the resulting crude methyl 2-(2-bromophenyl)-5-chloropentanoate (2.895 g) in ethanol (20 mL), and the reaction solution was stirred at room temperature for three hours. Hydrazine monohydrate (8 mL) was further added to the reaction solution, and the reaction solution was stirred at room temperature for two days. The reaction solution was concentrated under reduced pressure. Saturated sodium bicarbonate water and ethyl acetate and were added to the residue, and the organic layer was separated. The resulting organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 1.504 g of the crude purified title compound. The property value of the compound is as follows.

후처리

  1. temperaturecooling
  2. stirringfurther stirred at room temperature for 30 minutes
  3. temperatureice-cooled again
  4. stirringthe reaction solution was stirred at room temperature overnight
  5. customthe organic layer was separated
  6. washThe resulting organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1be60809ef304aff84399330119b80e9
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973033B2

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