Dichloromethane → 2-Chloro-3-(4-methoxyphenyl)propanal

HRID 1257768Notes

Reaction equation

HRID 1257768 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH:19]=[O:20])=[CH:13][CH:12]=1.ClCCl>N1CCC[C@@H]1C(O)=O>[Cl:1][CH:18]([CH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=1)[CH:19]=[O:20]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31398ChlorosuccinimideHCID 111266073-(4-Methoxyphenyl)propanal

Product 1

HCID 121027562-Chloro-3-(4-methoxyphenyl)propanalYield 71%

Reagents, catalysts & solvents 1

HCID 8988D-ProlineCatalyst

Procedure

N-Chlorosuccinimide (980 mg, 0.0073 mol) was added to a mixture of 3-(4-methoxyphenyl)propanal (1.0 g, 6.1 mmol) and D-proline (40 mg, 0.3 mmol) in dichloromethane (10 mL, 200 mmol) at 0° C. The reaction mixture was warmed to RT after 1 h, quenched with water, and extracted with dichloromethane. The organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate in hexanes to give the desired product (860 mg). 1H NMR (400 MHz, CDCl3): 9.52 (s, 1H), 7.18 (dd, 2H), 6.84 (dd, 2H), 4.36 (m, 1H), 3.80 (s, 3H), 3.32 (m, 1H), 3.02 (m, 1H).

Workup

  1. customquenched with water
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6fe530957cde4a378dcab99723ab0b77
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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