Bromide ion → 2-Bromo-1-(thiophen-2-yl)propan-1-one

HRID 1906161Notes

Reaction equation

HRID 1906161 reaction equation
[C:1]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)(=[O:4])[CH2:2][CH3:3].[Br:10]Br.[Br-].CCO>C(Cl)(Cl)(Cl)Cl.C(=S)=S>[Br:10][CH:2]([CH3:3])[C:1]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 259Bromide ionHCID 702EthanolHCID 24408BromineHCID 261792-Propionylthiophene

Product 1

HCID 117699522-Bromo-1-(thiophen-2-yl)propan-1-one

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolvent2×HCID 6348Carbon DisulfideSolvent

Procedure

An ice cold solution of 2-propionylthiophene (1.40 g) in carbon tetrachloride (25 ml) was treated with a solution of bromine (0.54 ml) in carbon tetrachloride (20 ml) over 5 mins. The resulting solution was then stirred at room temperature. After 1.5 h the mixture was evaporated to an amber oil (2.17 g). A portion of the oil (600 mg) was subjected to preparative thin-layer chromatography on silica developing with chloroform-petrol (b.p. 60°-80° C.) (1:4) (4 runs) and gave an amber oil, the title bromide (410 mg), λmax (EtOH) 272.5 nm (ε7,910), 294 nm (ε8,340), νmax (CS2) 1658, 713 cm-1.

Workup

  1. customAfter 1.5 h the mixture was evaporated to an amber oil (2.17 g)
  2. customgave an amber oil

Sources & evidence

ORD record
ord-05cd2f38281742f5b68765d126b8283f
Source dataset
uspto-grants-1987_03
Patent number
US04650800

Reaction notes

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