Dimethyl Disulfide → HCID 4913387, compound

HRID 1857998Notes

Reaction equation

HRID 1857998 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.C([Li])CCC.[CH3:19][S:20]SC.[OH-].[Na+]>O1CCCC1>[CH3:13][O:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([S:20][CH3:19])[CH:3]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 12232Dimethyl DisulfideHCID 14798Sodium HydroxideHCID 787862-Bromo-6-methoxynaphthaleneHCID 178418339Butyllithium

Product 1

HCID 4913387HCID 4913387, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-6-methoxynaphthalene (22.2 g, 93.6 mmol) in tetrahydrofuran (500 ml) was cooled to -78° C. and n-butyllithium (75 ml 1.6 M in THF, 121.7 mmol) was added dropwise over 15 minutes. After 0.5 h, dimethyl disulfide (13 ml, 140 mmol) was added and5 the reaction mixture was allowed to warm to room temperature. After 16 h, 1N sodium hydroxide (100 ml) was added and the reaction mixture was stirred for 1 h. The organic layer was separated and washed with 1N sodium hydroxide, 5% aqueous sodium sulfite, and brine, and dried over sodium sulfate. The solvent was removed in vacuo and the crude product was recrystallized form ethyl acetate and hexane to give 11.1 g of 2-methoxy-6-methylthionaphthalene as a solid (58% yield).

Workup

  1. waitAfter 16 h
  2. customThe organic layer was separated
  3. washwashed with 1N sodium hydroxide, 5% aqueous sodium sulfite, and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe crude product was recrystallized form ethyl acetate and hexane

Sources & evidence

ORD record
ord-0767438c2d884ef49d36dc78e9b4c12e
Source dataset
uspto-grants-2000_11
Patent number
US06150397

Reaction notes

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