3-(5-Bromo-4-chloro-2-methoxyphenyl)propanal → HCID 117607186, compound

HRID 588864Notes

Reaction equation

HRID 588864 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[Br:14][C:15]1[C:16]([Cl:27])=[CH:17][C:18]([O:25][CH3:26])=[C:19]([CH2:21][CH2:22][CH:23]=[O:24])[CH:20]=1>CC(C)=O>[Br:14][C:15]1[C:16]([Cl:27])=[CH:17][C:18]([O:25][CH3:26])=[C:19]([CH2:21][CH2:22][C:23]([OH:3])=[O:24])[CH:20]=1

Participants

4

Reactant 2

HCID 1176071873-(5-Bromo-4-chloro-2-methoxyphenyl)propanalHCID 131709961Jones' reagent

Product 1

HCID 117607186HCID 117607186, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of Jones reagent (3 mL, 5.4 mmol, 2.8 M) in acetone (20 mL), 3-(5-bromo-4-chloro-2-methoxyphenyl)propanal (860 mg, 3.1 mmol) was added. The reaction was stirred at RT for 12 h, quenched with iso-propylalcohol and then stirred for 10 min. The resulting mixture was diluted with water, extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=1:1) to afford the desired product (358 mg, 38% yield). ESI-MS m/z: 291.1[M+H]−.

Workup

  1. customquenched with iso-propylalcohol
  2. stirringstirred for 10 min
  3. additionThe resulting mixture was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=1:1)

Sources & evidence

ORD record
ord-fd328a5cfdf0405183d2f700670f88bc
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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