1-(Thiophen-3-yl)ethanone → 2-Bromo-1-(thiophen-3-yl)ethan-1-one

HRID 2248960Notes

Reaction equation

HRID 2248960 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>CCOCC>[Br:13][CH2:2][C:1]([C:4]1[CH:8]=[CH:7][S:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 151161-(Thiophen-3-yl)ethanoneHCID 24408BromineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27763792-Bromo-1-(thiophen-3-yl)ethan-1-oneYield 85.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Acetylthiophene (6.3 g, 50 mmol) was dissolved in anhydrous ether (100 ml) and aluminium chloride (catalytic amount) added. Bromine (2.55 ml, 50 mmol) was added dropwise and then stirred for 10 min. The ether was removed under reduced pressure and the residue washed with water. The crude product was recrystallised from petroleum-ether (60°-80° C.) to yield 3-bromoacetylthiophene m.p. 54°-56° C. (8.76 g, 85%), δH (CDCl3) 8.15(1H, dd, H2), 7.55(1H, dd, H4'), 7.35(1H, dd, H5').

Workup

  1. customThe ether was removed under reduced pressure
  2. washthe residue washed with water
  3. customThe crude product was recrystallised from petroleum-ether (60°-80° C.)

Sources & evidence

ORD record
ord-80798c9ad9b94d61a032fecf18f227c2
Source dataset
uspto-grants-1991_08
Patent number
US05041567

Reaction notes

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