Allyl bromide → HCID 14820506, compound

HRID 1088725Notes

Reaction equation

HRID 1088725 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[CH:18]=[CH2:19]>CC(C)=O>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH2:8][CH2:7][C:6]=2[CH:10]=1)[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 11367101Benzo[b]thiophene-5-ol, 2,3-dihydro-

Product 1

HCID 14820506HCID 14820506, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-hydroxy-2,3-dihydrobenzothiophene (1.53 g, 10.05 mmoles) in 200 mL acetone was added K2CO3 (12.5 g, 90.45 mmoles) with good mechanical stirring. The suspension was warmed and allyl bromide (4.86 g, 40.20 mmoles) was added in one portion. The reaction mixture was then heated to reflux overnight. After cooling, the solids were removed by filtration and the filtrate concentrated. The residue was taken up in 50/50 vol/vol hexane/methylene chloride and refiltered to remove the remaining salts. Concentration afforded 3.2 q crude product (a yellow oil) which was purified by flash chromatography (3% EtOAc in hexane to elute) to give 1.61 g pure product (83.4%) as an oil.

Workup

  1. temperatureThe suspension was warmed
  2. temperatureThe reaction mixture was then heated
  3. temperatureto reflux overnight
  4. temperatureAfter cooling
  5. customthe solids were removed by filtration
  6. concentrationthe filtrate concentrated
  7. customto remove the remaining salts
  8. concentrationConcentration
  9. customafforded 3.2 q crude product (a yellow oil) which
  10. customwas purified by flash chromatography (3% EtOAc in hexane to elute)

Sources & evidence

ORD record
ord-f0097dec01dd4648a6d02265a4057a28
Source dataset
uspto-grants-1990_10
Patent number
US04963580

Reaction notes

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