Diethylene Glycol → HCID 11032456, compound

HRID 1107524Notes

Reaction equation

HRID 1107524 reaction equation
[C:1]([C:4]1[S:5][C:6]2[C:13]([Br:14])=[CH:12][CH:11]=[CH:10][C:7]=2[C:8]=1[CH3:9])(=O)[CH3:2].C(O)COCCO.O.NN.[OH-].[K+]>O>[CH2:1]([C:4]1[S:5][C:6]2[C:13]([Br:14])=[CH:12][CH:11]=[CH:10][C:7]=2[C:8]=1[CH3:9])[CH3:2]

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 18787513HCID 18787513, compound

Product 1

HCID 11032456HCID 11032456, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

8.6 g (32 mmol) of 2-acetyl-3-methyl-7-bromobenzothiophene and 175 ml of diethylene glycol are placed in a 500 ml three-necked flask equipped with a distillation system. The mixture is stirred at 30° C. for 5 minutes and 4.2 ml (56 mmol) of hydrazine monohydrate are added dropwise. The mixture is heated at 40° C. for 5 minutes and 4.3 g (76.6 mmol) of powdered potassium hydroxide are added. The temperature is brought to 110° C. for 40 minutes and then to a 160° C. for 100 minutes, in order to allow the water present in the reaction mixture to be distilled off. The mixture, once cooled, is then poured onto crushed ice and extraction is carried out with ethyl acetate (3×200 ml). The organic phases are combined, washed with 200 ml of a saturated sodium bicarbonate solution and 2×200 ml of water, dried over magnesium sulphate and concentrated. The residue is purified by chromatography on a silica column (elution solvent: cyclohexane). 7.62 g (Yield: 84%) of 2-ethyl-3-methyl-7-bromobenzothiophene are obtained in the form of a yellow oil.

Workup

  1. customequipped with a distillation system
  2. temperatureThe mixture is heated at 40° C. for 5 minutes
  3. waitThe temperature is brought to 110° C. for 40 minutes
  4. waitto a 160° C. for 100 minutes
  5. distillationto be distilled off
  6. temperatureThe mixture, once cooled
  7. additionis then poured
  8. customonto crushed
  9. extractionice and extraction
  10. washwashed with 200 ml of a saturated sodium bicarbonate solution and 2×200 ml of water
  11. dry with materialdried over magnesium sulphate
  12. concentrationconcentrated
  13. customThe residue is purified by chromatography on a silica column (elution solvent: cyclohexane)

Sources & evidence

ORD record
ord-ee8376c555954f5680ab147383b1dfbe
Source dataset
uspto-grants-2000_05
Patent number
US06060508

Reaction notes

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