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1-Bromo-3-chloropropane → 5-Chloro-2-(4-chlorophenyl)pentanoic acid

HRID 599644
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HRID 599644 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C([Li])CCC.Br[CH2:18][CH2:19][CH2:20][Cl:21].C(OCC)(=O)C>C1COCC1>[Cl:21][CH2:20][CH2:19][CH2:18][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:9]([OH:11])=[O:10]
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참가 물질

6

반응물 4

HCID 80061-Bromo-3-chloropropaneHCID 8857Ethyl AcetateHCID 15880(4-Chlorophenyl)acetic acidHCID 178418339Butyllithium

생성물 1

HCID 670673305-Chloro-2-(4-chlorophenyl)pentanoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A solution of 4-chlorophenylacetic acid (1 g) in THF (30 mL) was stirred at −78° C. for 20 minutes. n-Butyl lithium (2.66 M solution in hexane, 4.41 mL) was added to the solution, and the reaction solution was stirred at −78° C. for one hour. Thereafter, the reaction solution was stirred at 0° C. for one hour, 1-bromo-3-chloropropane (0.638 mL) was added to the reaction solution, and the reaction solution was stirred at room temperature for 18 hours. Thereafter, ethyl acetate and 1 N aqueous 2hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 1.55 g of the title compound. The property values of the compound are as follows.

후처리

  1. stirringThereafter, the reaction solution was stirred at 0° C. for one hour
  2. stirringthe reaction solution was stirred at room temperature for 18 hours
  3. customthe organic layer was separated
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6eb0cff0bc4c478db6b8004a768bfdc4
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07897632B2

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