Water → 4-Butylthiobenzaldhyde

HRID 2373140Notes

Reaction equation

HRID 2373140 reaction equation
[CH2:1]([S:5]C1C=CC(Br)=CC=1)[CH2:2][CH2:3]C.[Li][CH2:14][CH2:15][CH2:16][CH3:17].CN(C=O)C.O.[CH2:24]1[CH2:28]O[CH2:26][CH2:25]1>>[CH2:14]([C:24]1[CH:28]=[CH:3][C:2]([CH:1]=[S:5])=[CH:26][CH:25]=1)[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 14418074(4-Bromophenyl)(butyl)sulfaneHCID 178418339Butyllithium

Product 1

HCID 190917074-Butylthiobenzaldhyde

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-bromophenyl n-butyl sulfide (1.5 g, 6.12 mmol) in 60 ml of dry THF was added nBuLi (4.1 ml, 1.6 M in hexanes) at −78° C. under nitrogen. The mixture was stirred for 1 hour at −78° C. and then DMF (2.0 ml) was added. The reaction mixture was stirred at room temperature for 2 hours. Then 40 ml of water was added to this mixture, the product was extracted three times by ether (3×50 ml) and the combined organic layer was dried over magnesium sulfate. After removal of solvent under reduced pressure, the product was purified by flash chromatography column using 10% of ethyl acetate in hexanes as eluant and isolated in 66.7% (0.88 g) yield.1H NMR (CDCl3, 500 MHz) δppm: 9.98 (s, 1H, CHO), 7.77 (d, J=8.5 Hz, 2H), 7.36 (d, J=8.5 Hz, 2H,), 7.11 (s, 2H), 3.02 (t, J=7.2 Hz, 2H, CH2), 1.71 (m, 2H, CH2), 1.50 (m, 2H, CH2), 0.97 (t, J=7.5 Hz, 6H, CH3).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. extractionthe product was extracted three times by ether (3×50 ml)
  3. dry with materialthe combined organic layer was dried over magnesium sulfate
  4. customAfter removal of solvent under reduced pressure
  5. customthe product was purified by flash chromatography column
  6. customisolated in 66.7% (0.88 g)
  7. customyield

Sources & evidence

ORD record
ord-77d3a63bde484380b78001c4be4e39ec
Source dataset
uspto-grants-2008_12
Patent number
US07459106B2

Reaction notes

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