Acetyl chloride → HCID 18787513, compound

HRID 1107523Notes

Reaction equation

HRID 1107523 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([Br:11])[C:5]=2[S:4][CH:3]=1.[C:12](Cl)(=[O:14])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[C:12]([C:3]1[S:4][C:5]2[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]=1[CH3:1])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 177500357-Bromo-3-methyl-1-benzothiophene

Product 1

HCID 18787513HCID 18787513, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

7.6 g (39.46 mmol) of 3-methyl-7-bromobenzothiophene (dried beforehand under vacuum over phosphorus pentoxide) and 70 ml of dichloromethane are placed in a 250 ml three-necked flask equipped with a thermometer. The mixture is cooled to 0° C. by an ice bath, 2.89 g (36.8 mmol) of acetyl chloride are added and then the reaction mixture is stirred for 5 minutes at 0 °C. 5 g of aluminium chloride are then added in small portions, the temperature being controlled so that it does not exceed 70° C., and stirring is continued at 0° C. for 45 minutes. The reaction mixture is poured onto crushed ice and extraction is carried out with ethyl acetate (3×150 ml). The organic phases are combined, washed with a saturated sodium bicarbonate solution (200 ml) and water (200 ml), dried over magnesium sulphate and then concentrated. The residue is purified by chromatography on a silica column (elution solvent: 5% ethyl acetate in petroleum ether). 8.55 g (Yield: 95%) of 2-acetyl-3-methyl-7-bromobenzothiophene are obtained in the form of a white solid. M.p.=105-107° C.

Workup

  1. customequipped with a thermometer
  2. customdoes not exceed 70° C.
  3. stirringstirring
  4. waitis continued at 0° C. for 45 minutes
  5. additionThe reaction mixture is poured
  6. customonto crushed
  7. extractionice and extraction
  8. washwashed with a saturated sodium bicarbonate solution (200 ml) and water (200 ml)
  9. dry with materialdried over magnesium sulphate
  10. concentrationconcentrated
  11. customThe residue is purified by chromatography on a silica column (elution solvent: 5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-a29f88ae659640c284a8d0cde28d0ca9
Source dataset
uspto-grants-2000_05
Patent number
US06060508

Reaction notes

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