Bromine → HCID 19001639, compound

HRID 486943Notes

Reaction equation

HRID 486943 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)([CH3:3])[CH3:2].[Br:13]Br.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:13][C:12]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][C:6]2[O:10][CH2:9][O:8][C:7]=2[CH:11]=1

Participants

6

Reactant 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 13934185HCID 13934185, compound

Product 1

HCID 19001639HCID 19001639, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
10 °C

Procedure

2.94 g of 5-isopropyl-1,3-benzodioxole was dissolved in 30 ml of carbon tetrachloride to obtain a solution. A solution of 3.15 g of bromine in 5 ml of carbon tetrachloride was dropwise added to the solution at a temperature of -5° to 5° C. The obtained mixture was stirred at 10° C. for 8.5 hours. Nitrogen gas was passed through the resulting mixture, followed by the addition of a saturated aqueous solution of sodium hydrogencarbonate and an aqueous solution of sodium thiosulfate. The obtained mixture was extracted with chloroform and the organic layer was washed with a saturated aqueous solution of common salt, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to obtain 4.38 g of the title compound as a crude oil. 1H-NMR (90 MHz, CDCl3) δ; 1.18(d, J=7.2 Hz, 6H), 3.31(sept, J=7.2 Hz, 1H), 5.88(s, 2H), 6.70(s, 1H), 6.91(s, 1H).

Workup

  1. customto obtain a solution
  2. extractionThe obtained mixture was extracted with chloroform
  3. washthe organic layer was washed with a saturated aqueous solution of common salt
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-88b19c9f7e834f599d50521e262ad82f
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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