Sodium methanethiolate → 6-Methylsulfanylbenzo[b]thiophene

HRID 1986208Notes

Reaction equation

HRID 1986208 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.[CH3:11][S-:12].[Na+]>CN(C=O)C>[CH3:11][S:12][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 127444006-Bromo-benzo[b]thiophene

Product 1

HCID 198037266-Methylsulfanylbenzo[b]thiopheneYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-bromobenzo[b]thiophene (2.0 g, 9.4 mmol) and sodium thiomethoxide (1.30 g, 18.8 mmol) in DMF (15 mL) is stirred at 90° C. under nitrogen for 6 hours. The reaction is cooled to room temperature, extracted with ethyl acetate and saturated aqueous sodium chloride, washed with 2 N aqueous NaOH solution, saturated aqueous sodium chloride, dried over Na2SO4, filtered, and evaporated. The residue is purified by chromatography on silica gel, eluting with ethyl acetate:hexanes 3:7, to give the title product as a red liquid (1.41 g) which is used for next reaction without further purification.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. extractionextracted with ethyl acetate and saturated aqueous sodium chloride
  3. washwashed with 2 N aqueous NaOH solution, saturated aqueous sodium chloride
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by chromatography on silica gel
  8. washeluting with ethyl acetate:hexanes 3:7

Sources & evidence

ORD record
ord-83d3ffda27a649bfb8c37423a07d4f9b
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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