Bromine → HCID 17980974, compound

HRID 2219997Notes

Reaction equation

HRID 2219997 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([CH3:11])[S:8][C:7]=2[CH:12]=1.[Br:13]Br>C(Cl)(Cl)Cl>[Br:13][C:10]1[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:12][C:7]=2[S:8][C:9]=1[CH3:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 221434866-Methoxy-2-methylbenzo[b]thiophene

Product 1

HCID 17980974HCID 17980974, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 20.63 g (0.13 mol) of 6-Methoxy-2-methylbenzo[b]thiophene and 250 mL of CHCl3 is cooled by using a ice-water bath. A solution consisting of 20.08 g (0.14 mol) of Br2 and 90 mL of CHCl3 is added dropwise. After the addition is completed, the mixture is stirred for 30 min at room temperature and then hydrolysed with 300 mL of saturated aqueous Na2S2O6 solution. The aqueous phase is extracted twice with 300 mL of CHCl3. The combined organic phases are washed several times with water, dried over magnesium sulfate and then are concentrated under reduced pressure. The resulting solid recrystallised from methanol gives a white solid (28.50 g, 88% yield).

Workup

  1. temperatureis cooled
  2. additionis added dropwise
  3. additionAfter the addition
  4. extractionThe aqueous phase is extracted twice with 300 mL of CHCl3
  5. washThe combined organic phases are washed several times with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationare concentrated under reduced pressure
  8. customThe resulting solid recrystallised from methanol

Sources & evidence

ORD record
ord-6547a7d12c544040885403e15a318cb9
Source dataset
uspto-grants-2008_08
Patent number
US07416682B2

Reaction notes

Loading…