Bromine → HCID 59509366, compound

HRID 452670Notes

Reaction equation

HRID 452670 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Br:14]Br>C(O)(=O)C.C(OCC)(=O)C>[Br:14][C:3]1[C:4]2[CH:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:6][C:5]=2[S:1][CH:2]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 15209278Methyl benzo[b]thiophene-5-carboxylate

Product 1

HCID 59509366HCID 59509366, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 1-benzothiophene-5-carboxylate (5.15 g, 26.8 mmol) in acetic acid (50 mL) was added dropwise bromine (2.06 mL, 40.2 mmol) at room temperature, and the resulting mixture was stirred for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with 1 M aqueous sodium sulfite solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1), and crystallized from hexane/ethyl acetate to give the title compound (6.20 g, yield 85%) as colorless crystals.

Workup

  1. washwashed with 1 M aqueous sodium sulfite solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)
  5. customcrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-084fd9b621164e1ba2799e786602fb28
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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