Hydrochloric Acid → HCID 90308862, compound

HRID 2283672Notes

Reaction equation

HRID 2283672 reaction equation
[C:1](OC)(=O)[CH2:2][SH:3].C(=O)([O-])[O-].[K+].[K+].[Br:13][C:14]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18](Br)[C:15]=1C=O.Cl>CS(C)=O>[Br:13][C:14]1[C:15]2[CH:18]=[CH:19][S:3][C:2]=2[CH:1]=[C:20]([CH3:22])[CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 129827482,6-Dibromo-4-methylbenzaldehyde

Product 1

HCID 90308862HCID 90308862, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

Methyl thioglycolate (0.060 ml) and potassium carbonate (190 mg) were added to a solution of 2,6-dibromo-4-methylbenzaldehyde (153 mg) in dimethylsulfoxide (1.7 mL), and the reaction solution was stirred at 120° C. for 7 hours. The reaction solution was neutralized with 2 M hydrochloric acid, extracted with ethyl acetate, and washed with a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. A 5 M aqueous sodium hydroxide solution (0.8 ml) was added to a solution of the resultant residue in a mixture of THF-methanol (1:1) (3.2 ml), and the reaction solution was stirred at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate, and washed successively with 2 M hydrochloric acid and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. Silver carbonate (30 mg) and acetic acid (0.005 ml) were added to a solution of the resultant residue in dimethylsulfoxide (1.1 mL), and the reaction solution was stirred at 120° C. for 6 hours. The reaction solution was diluted with ethyl acetate, and washed successively with an aqueous sodium bicarbonate solution and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate) to obtain 4-bromo-6-methylbenzo[b]thiophene.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with a saturated saline solution
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under vacuum
  5. additionA 5 M aqueous sodium hydroxide solution (0.8 ml) was added to a solution of the resultant residue in a mixture of THF-methanol (1:1) (3.2 ml)
  6. stirringthe reaction solution was stirred at room temperature for 2 hours
  7. additionThe reaction solution was diluted with ethyl acetate
  8. washwashed successively with 2 M hydrochloric acid
  9. dry with materialAfter drying over anhydrous sodium sulfate
  10. customthe solvent was evaporated under vacuum
  11. additionSilver carbonate (30 mg) and acetic acid (0.005 ml) were added to a solution of the resultant residue in dimethylsulfoxide (1.1 mL)
  12. stirringthe reaction solution was stirred at 120° C. for 6 hours
  13. additionThe reaction solution was diluted with ethyl acetate
  14. washwashed successively with an aqueous sodium bicarbonate solution
  15. dry with materialAfter drying over anhydrous sodium sulfate
  16. customthe solvent was evaporated under vacuum
  17. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f04495a27d944531b9cc2c169b80ac99
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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