Bromine → 4-Bromo-2-propionylthiophene

HRID 2258076

Reaction equation

HRID 2258076 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:9])[CH2:7][CH3:8].[Al+3].[Cl-].[Cl-].[Cl-].[Br:14]Br>C(Cl)(Cl)Cl>[Br:14][C:4]1[CH:3]=[C:2]([C:6](=[O:9])[CH2:7][CH3:8])[S:1][CH:5]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 261792-PropionylthiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 8189324-Bromo-2-propionylthiophene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A 47.3 g (338 mmol) sample of 1-(2-thienyl)-1-propanone (Aldrich) was dissolved in 225 mL of CHCl3 and 101.3 g (760 mmol) of AlCl3 was added with stirring. To this mixture was added a solution of bromine (57.5 g, 360 mmol) in 375 mL of CHCl3. The mixture was stirred at room temperature over night then poured into 500 mL of ice water. The organic layer was separated, washed with water (2×200 mL), dried over MgSO4, filtered and evaporated to yield 81 g of the crude title compound, which was taken directly to the next step. mp 40°-41° C.; MS: 158 (M+H)+, 236 (M+NH4)+ ; NMR (CDCl3) δ: 1.22 (t, 3H, J=7.5 Hz), 2.91 (q, 2H, J=7.5Hz), 7.51 (d, 1H), 7.60 (d, 1H). IR (KBr): 2960, 1670, 1400, 1220 cm-1.

Workup

  1. stirringThe mixture was stirred at room temperature over night
  2. customThe organic layer was separated
  3. washwashed with water (2×200 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3a5da5033c474312aaa7befb256507b1
Source dataset
uspto-grants-1997_08
Patent number
US05659037

Linked notes

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