Acetyl chloride → 1-(5-Bromo-4-methylthiophen-2-yl)ethan-1-one

HRID 242398Notes

Reaction equation

HRID 242398 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].[Br:9][C:10]1[S:11][CH:12]=[CH:13][C:14]=1[CH3:15]>ClCCl>[Br:9][C:10]1[S:11][C:12]([C:1](=[O:3])[CH3:2])=[CH:13][C:14]=1[CH3:15]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 843142-Bromo-3-methylthiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 454803531-(5-Bromo-4-methylthiophen-2-yl)ethan-1-oneYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (7.09 g) is added to a suspension of AlCl3 (11.53 g) in dichloromethane (310 ml) at 0° C. After 45 minutes at 0° C., 2-bromo-3-methylthiophene (5.0 g) is added dropwise. After 1 hour at 0° C., the reaction is quenched by added water (100 ml). The mixture is extracted three times with dichloromethane. The organic phases are combined, dried over MgSO4 and concentrated in vacuo. The crude product is purified by chromatography on silica gel (180 g) eluting with a mixture of ethyl acetate and heptane (1:6) to yield 1-(5-bromo-4-methyl-thiophen-2-yl)-ethanone (3.5 g) as a brown solid.

Workup

  1. waitAfter 1 hour at 0° C.
  2. customthe reaction is quenched
  3. additionby added water (100 ml)
  4. extractionThe mixture is extracted three times with dichloromethane
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by chromatography on silica gel (180 g)
  8. washeluting with a mixture of ethyl acetate and heptane (1:6)

Sources & evidence

ORD record
ord-867965c46b404420bd394b02d533937e
Source dataset
uspto-grants-2014_02
Patent number
US08653116B2

Reaction notes

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