Hydrogen Bromide → 3-Bromomethyl-5-methylbenzo[b]thiophene

HRID 1816534Notes

Reaction equation

HRID 1816534 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:10][C:11]#[CH:12])=O)=[CH:4][CH:3]=1.[BrH:13].O>O1CCOCC1>[Br:13][CH2:12][C:11]1[C:6]2[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[S:8][CH:10]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 117886144-Methyl-1-(prop-2-ynylsulfinyl)benzene

Product 1

HCID 121113773-Bromomethyl-5-methylbenzo[b]thiopheneYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In 110 mL of dioxane, was dissolved 7.18 g (40.3 mmol) of the compound obtained in Example 11. The resulting solution was refluxed at 100° C. for 100 minutes The refluxed solution was then cooled, and 7.42 g (44 mmol) of a 48% hydrobromic acid was added. The obtained mixture was allowed to stand at room temperature for 1 hour. Water was then added, and the obtained mixture was extracted with ethyl acetate. The resulting extract was dried with magnesium sulfate and vacuum concentrated to provide 9.04 g of 3-(bromomethyl)-5-methylbenzo[b]thiophene. The yield was 93%.

Workup

  1. temperaturewas then cooled
  2. extractionthe obtained mixture was extracted with ethyl acetate
  3. extractionThe resulting extract
  4. dry with materialwas dried with magnesium sulfate and vacuum
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e79ac6ef91ba4612a52a5af4f35a041d
Source dataset
uspto-grants-2005_04
Patent number
US06884896B2

Reaction notes

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