Bromine → Ethyl 5-bromo-6-(5-chloro-2-thienyl)-6-oxohexanoate

HRID 747447

Reaction equation

HRID 747447 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:17])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.[Br:18]Br.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:18][CH:8]([C:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:17])[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 24437Sodium SulfiteHCID 18174688Ethyl 6-(5-chloro-2-thienyl)-6-oxohexanoate

Product 1

HCID 18174681Ethyl 5-bromo-6-(5-chloro-2-thienyl)-6-oxohexanoateYield 118.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 6-(5-chloro-2-thienyl)-6-oxohexanoate (50.0 g) was dissolved in methylene chloride (150 ml), to which was added dropwise bromine (24.5 g) with stirring at room temperature. The mixture was stirred at room temperature for 1 hour, a 10% aqueous solution of sodium sulfite was then carefully added until disappearance of the red color of bromine, which was extracted with diethyl ether (200 ml×2). The organic layer was washed with a 10% aqueous solution of sodium hydrogen carbonate (100 ml), dried over anhydrous magnesium sulfate, and concentrated to give ethyl 5-bromo-6-(5-chloro-2-thienyl)-6-oxohexanoate as an oil (64.4 g, >99%).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. extractionwas extracted with diethyl ether (200 ml×2)
  3. washThe organic layer was washed with a 10% aqueous solution of sodium hydrogen carbonate (100 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f5daf739074f4c5dab8244ba26a9e1ca
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Linked notes

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