Water → HCID 13663050, compound

HRID 280597Notes

Reaction equation

HRID 280597 reaction equation
C([Li])CCC.Br[C:7]1[C:8]2[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1.[CH3:17][S:18]SC.O>CCCCCC.CCOCC>[Br:16][C:14]1[CH:13]=[CH:12][C:9]2[S:10][CH:11]=[C:7]([S:18][CH3:17])[C:8]=2[CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 12232Dimethyl DisulfideHCID 6261613,5-dibromobenzo[b]thiopheneHCID 178418339Butyllithium

Product 1

HCID 13663050HCID 13663050, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of n-butyl-lithium in hexane (35 ml of 1.55M solution) was added dropwise to a stirred solution of 3,5-dibromobenzo[b]thiophene (14.6 g) in dry ether (600 ml) at -70° C. under dry nitrogen. The mixture was stirred at -70° C. for 30 minutes and then a solution of dimethyl disulphide (4.90 g) in 10 ml of dry ether was added with stirring over 5 minutes. The resulting mixture was stirred at -70° C. for 4 hours and then allowed to warm up to room temperature. Water (50 ml) was added and the organic layer was separated, washed with water and dried (Na2SO4). Evaporation of the ether gave an oil which was chromatographed on silica gel. Elution with petrol (b.p. 40°-60°) gave a small amount of impurity followed by pure product. The product-containing fractions were evaporated and the residue was distilled to give 5-bromo-3-methylthiobenzo[b]thiophene (10.36 g), b.p. 140°-144° @ 0.6 mm, m.p. 56°-57°.

Workup

  1. stirringwith stirring over 5 minutes
  2. stirringThe resulting mixture was stirred at -70° C. for 4 hours
  3. temperatureto warm up to room temperature
  4. customthe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the ether
  8. customgave an oil which
  9. customwas chromatographed on silica gel
  10. washElution with petrol (b.p. 40°-60°)
  11. customgave a small amount of impurity
  12. customThe product-containing fractions were evaporated
  13. distillationthe residue was distilled

Sources & evidence

ORD record
ord-ab44f12611e84cd298247c15312e7b15
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

Loading…