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

HRID 1816535Notes

Reaction equation

HRID 1816535 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]>C(OCCC)(=O)C>[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

4

Reactant 2

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

Product 1

HCID 121113773-Bromomethyl-5-methylbenzo[b]thiopheneYield 88%

Reagents, catalysts & solvents 1

HCID 7997Propyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In 445 mL of propyl acetate, was dissolved the compound obtained in Example 11 (29.7 g, 167 mmol). The resulting solution was heated at 100° C. for 1 hour. The solution was then cooled with ice to keep the internal temperature of the reaction system at 10° C. To the cooled solution, was added 22.8 mL of a 48% hydrobromic acid. The obtained mixture was allowed to stand under cooling with ice for 1 hour and 30 minutes. The aqueous layer was separated, and the organic layer was washed with 50 mL of water, dried with magnesium sulfate, vacuum concentrated and dried to obtain 35.3 g of a brown transparent oil 3-(bromomethyl)-5-methylbenzo[b]thiophene. (yield=88%).

Workup

  1. temperatureThe solution was then cooled with ice
  2. customat 10° C
  3. temperatureunder cooling with ice for 1 hour and 30 minutes
  4. customThe aqueous layer was separated
  5. washthe organic layer was washed with 50 mL of water
  6. dry with materialdried with magnesium sulfate, vacuum
  7. concentrationconcentrated
  8. customdried

Sources & evidence

ORD record
ord-a011e17be91b46e3ab616c1e69a276d6
Source dataset
uspto-grants-2005_04
Patent number
US06884896B2

Reaction notes

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