Dimethyl Sulfoxide → 2-Chloro-4-(pyrrolidin-1-yl)benzaldehyde

HRID 2278210Notes

Reaction equation

HRID 2278210 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[Cl:1][C:2]1[CH:9]=[C:8]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 1450242-Chloro-4-fluorobenzaldehyde

Product 1

HCID 71486202-Chloro-4-(pyrrolidin-1-yl)benzaldehydeYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 100 mL round-bottom flask was charged with 2-chloro-4-fluorobenzaldehyde (2.50 g, 15.8 mmol, 1.00 equiv), pyrrolidine (2.20 g, 30.9 mmol, 2.00 equiv), potassium carbonate (4.40 g, 31.8 mmol, 2.00 equiv), DMSO (50 mL). The resulting solution was stirred overnight at 100° C., diluted with H2O (50 mL), extracted with ethyl acetate (3×30 mL). The organic layers were combined and washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (20/80) to provide 2.40 g (73% yield) of 2-chloro-4-(pyrrolidin-1-yl)benzaldehyde as a yellow solid. LCMS: (ESI, m/z): 210 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. washwashed with brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (20/80)

Sources & evidence

ORD record
ord-b50fed07fce2430f9c9ece4b1119e733
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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