Isopropanol → 4-Bromo-alpha-phenylbenzeneacetic acid

HRID 509193노트

반응식

HRID 509193 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[O:10])=[CH:4][CH:3]=1.CC(C)=[O:19].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:9]([OH:19])=[O:10])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 3776IsopropanolHCID 125551782-(4-Bromophenyl)-2-phenylacetaldehydeHCID 131709961Jones' reagent

생성물 1

HCID 38473074-Bromo-alpha-phenylbenzeneacetic acid수율 36%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a stirring solution of compound 52 (5.27 g, 19.15 mmol) in acetone (60 mL) cooled to −10° C. was added Jones Reagent (2.93 mL, 2.5 M solution) drop wise. Isopropyl alcohol was then added until the reaction mixture turned green. The mixture was filtered through Celite, diluted with ethyl acetate and washed with NaOH. The organic layer was discarded and the aqueous layer was acidified with 1M HCl to pH 1 and further extracted with ethyl acetate. The combined organics were dried over Na2SO4, filtered and concentrated to afford 2-(4-bromophenyl)-2-phenylacetic acid 53 (2 g, 36%) as a beige solid.

후처리

  1. filtrationThe mixture was filtered through Celite
  2. additiondiluted with ethyl acetate
  3. washwashed with NaOH
  4. extractionfurther extracted with ethyl acetate
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-cb98c5ac26e3467eb133816dbb14f7e3
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096565B2

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