Hydrochloric Acid → 4-(Benzylsulfanyl)benzaldehyde

HRID 1644694Notes

Reaction equation

HRID 1644694 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([SH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.F[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.Cl>O.CN(C=O)C>[CH2:7]([S:14][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7509Benzyl mercaptanHCID 10796Cesium carbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 128424604-(Benzylsulfanyl)benzaldehydeYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred mixture of cesium carbonate (12.81 g, 39.33 mmol), benzyl mercaptan (4.7 mL, 39 mmol), and N,N,-dimethylformamide (80 mL) was added 4-fluorobenzaldehyde, slowly over several minutes. The reaction mixture was stirred at 40° C. overnight. The reaction mixture was cooled to room temperature, then diluted with water (500 mL). The resulting mixture was acidified to pH 4 using 1 N aqueous HCl, then extracted with ethyl acetate (3×150 mL). The combined organic layers were washed with water and brine, dried over MgSO4, filtered, and concentrated. A solution of the crude product and dichloromethane was concentrated over silica gel, and the resulting silica gel supported crude product was loaded onto an Analogix SuperFlash™ column. Flash chromatography (100% hexanes -15% ethyl acetate in hexanes) afforded 7.70 g (90%) of 4-(benzylsulfanyl)-benzaldehyde as a slightly pink solid.

Workup

  1. waitslowly over several minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate (3×150 mL)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationA solution of the crude product and dichloromethane was concentrated over silica gel

Sources & evidence

ORD record
ord-2186377eb5b0417fb59f3382efc8300c
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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