Dimethyl Disulfide → HCID 86669336, compound

HRID 401180Notes

Reaction equation

HRID 401180 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:12][CH3:13])[C:9]=1[OH:10])[CH:5]=[O:6].[CH3:14][S:15]SC>N1C=CC=CC=1>[CH2:12]([O:11][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([S:15][CH3:14])[C:9]=1[OH:10])[CH:5]=[O:6])[CH3:13]

Participants

4

Reactant 2

HCID 12232Dimethyl DisulfideHCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehyde

Product 1

HCID 86669336HCID 86669336, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

To the solution of 3-bromo-5-ethoxy-4-hydroxybenzaldehyde (1.00 g, 4.08 mmol) in pyridine (10 mL) was added Cu powder (0.52 g, 8.1 mmol) and methyl disulfide (0.77 g, 8.2 mmol), the mixture was then heated at 90° C. overnight. The reaction mixture was filtered, and the solvent was removed under reduced pressure, the residue was poured into water, and 6 N HCl (5 mL) was added, then the mixture was extracted with DCM (50 mL×3), the combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel column (PE:EA=5:1) to give Intermediate 50 (600 mg, yield 69%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under reduced pressure
  3. additionthe residue was poured into water, and 6 N HCl (5 mL)
  4. additionwas added
  5. extractionthe mixture was extracted with DCM (50 mL×3)
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column (PE:EA=5:1)

Sources & evidence

ORD record
ord-f11bbd39b8274de0938264e485418433
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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