3-(4-Bromophenyl)propionic acid → 1-Indanone, 6-bromo-

HRID 472953

반응식

HRID 472953 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>O=S(Cl)Cl.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][CH2:9][C:10]2=[O:12])=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 27356093-(4-Bromophenyl)propionic acidHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 1397781-Indanone, 6-bromo-수율 473.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 24386Thionyl Chloride용매

실험 절차

A mixture of 3-(4-bromophenyl)propanoic acid (26 g, 12 mmol) in SOCl2 (50 mL) was refluxed overnight, the mixture was concentrated, then added to AlCl3 (80 g, 61 mmol) in DCM (100 mL), the mixture was stirred at room temperature overnight. The mixture was quenched with HCl aqueous, extracted with DCM, washed with brine, dried over Na2SO4, concentrated to give 6-bromo-indan-1-one (12 g, 48%). 1H-NMR (CD3OD): 2.65 (m, 2H), 3.06 (m, 2H), 7.31 (m, 1H), 7.62 (m, 1H), 7.80 (m, 1H).

후처리

  1. temperaturewas refluxed overnight
  2. concentrationthe mixture was concentrated
  3. customThe mixture was quenched with HCl aqueous
  4. extractionextracted with DCM
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-048863f3e19545faafea1de964a80668
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633212B2

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