Dimethyl Disulfide → HCID 19756807, compound

HRID 1588009Notes

Reaction equation

HRID 1588009 reaction equation
C([Li])CCC.Br[C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=2)=[CH:10][CH:11]=1.[CH3:19][S:20]SC.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH3:19][S:20][C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 12232Dimethyl DisulfideHCID 25517Ammonium ChlorideHCID 19006175HCID 19006175, compoundHCID 178418339Butyllithium

Product 1

HCID 19756807HCID 19756807, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 2.5M solution of n-butyllithium (2.2 mL; 5.5. mM) was slowly added to a solution of 2-bromo-5-(3'-bromophenyl)thiophene (1.59 g; 5 mM) in 10 mL of tetrahydrofuran at -78° under nitrogen. The mixture was stirred 10 mins. and dimethyldisulfide (1.35 mL; 15 mM) was added slowly. This mixture was stirred overnight at R.T. after which 5 mL of sat'd. ammonium chloride and 15 mL of ethyl acetate were added. The organic phase was separated, washed with 2×5 mL of sat'd. sodium chloride, and dried over anhyd. magnesium sulfate. Solvent removal and purification on silica gel with hexane as solvent gave 2-methylthio-5-(3'-bromophenyl)thiophene as a colorless oil boiling at 142°-5°/0.5 mm.

Workup

  1. stirringThis mixture was stirred overnight at R.T. after which 5 mL of sat'd
  2. customThe organic phase was separated
  3. washwashed with 2×5 mL of sat'd
  4. dry with materialsodium chloride, and dried over anhyd
  5. customSolvent removal and purification on silica gel with hexane as solvent

Sources & evidence

ORD record
ord-eaa3ca4c4aff46fdb4cfb6d6e9ee1ad6
Source dataset
uspto-grants-1993_06
Patent number
US05220011

Reaction notes

Loading…