Dimethyl Disulfide → HCID 19386774, compound

HRID 2399268Notes

Reaction equation

HRID 2399268 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])C=O.[CH2:14]([Li])CCC.CS[S:21][CH3:22].[Cl-].[NH4+]>C1COCC1>[CH3:13][O:12][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([CH3:14])[C:9]=1[O:10][CH3:11])[CH:22]=[S:21]

Participants

6

Reactant 4

HCID 12232Dimethyl DisulfideHCID 25517Ammonium ChlorideHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 19386774HCID 19386774, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-4,5-dimethoxybenzaldehyde (4.9 g) in THF (30 ml) was added over 10 minutes and the mixture cooled to 31 75° . Further n-butyllithium (20 ml) was then added, and the mixture stirred at -75° for 80 minutes, before adding dimethyldisulphide (2.7 g) by syringe. The mixture was stirred for 1.5 hours, allowing the temperature to rise to ambient, then treated with an aqueous solution of ammonium chloride (50 ml) and the organic layer separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers washed with brine, and dried over NaSO4. Crude product was purified by chromatography on silica, eluting with 10% ethyl acetate in hexane, to give 3,4-dimethoxy-5-methylthiobenzaldehyde (3.4 g): NMR (CDCl3): δ2.49 (s, 3H); 3.94 (s, 3H); 3.96 (s, 3H); 7.25 (d, 1H); 7.28 (d, 1H); 9.89 (s, 1H).

Workup

  1. temperaturethe mixture cooled to 31 75°
  2. stirringThe mixture was stirred for 1.5 hours
  3. customthe organic layer separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layers washed with brine
  6. dry with materialdried over NaSO4
  7. customCrude product was purified by chromatography on silica
  8. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-044336c2d8a54ec9aa412f93c000e596
Source dataset
uspto-grants-1995_09
Patent number
US05447925

Reaction notes

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