Sodium Carbonate → 2-Bromo-1-(thiophen-3-yl)ethan-1-one

HRID 554205Notes

Reaction equation

HRID 554205 reaction equation
[C:1]([C:4]1[CH:8]=[CH:7][S:6][CH:5]=1)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[Br:13]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)C>[Br:13][CH2:2][C:1]([C:4]1[CH:8]=[CH:7][S:6][CH:5]=1)=[O:3]

Participants

6

Procedure

To a solution of 3-acetylthiophene (3.73 g) in diethyl ether (60 mL) was added aluminum chloride (386 mg), and the mixture was stirred for 5 min. Bromine (1.55 mL) was slowly added at room temperature to this mixture, and the mixture was further stirred for 2 hr. Aqueous sodium carbonate solution was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was dried over anhydrous sodium sulfate, filtrated, and concentrated under reduced pressure. The residue was recrystallized from diisopropyl ether to give the title compound as white crystals (yield 3.93 g, 65%).

Workup

  1. stirringthe mixture was further stirred for 2 hr
  2. extractionthe mixture was extracted with diethyl ether
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-35e881a461574aa785a5d3669429b970
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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