Isopropanol → 4-Bromo-alpha-phenylbenzeneacetic acid

HRID 509193Notes

Reaction equation

HRID 509193 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 38473074-Bromo-alpha-phenylbenzeneacetic acidYield 36%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cb98c5ac26e3467eb133816dbb14f7e3
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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