Bromine → Isoxazole, 3-[3-bromo-2-methyl-6-(methylthio)phenyl]-4,5-dihydro-

HRID 49668Notes

Reaction equation

HRID 49668 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH3:9])[C:3]=1[C:10]1[CH2:14][CH2:13][O:12][N:11]=1.[Br:15]Br>S(=O)(=O)(O)O>[Br:15][C:7]1[C:2]([CH3:1])=[C:3]([C:10]2[CH2:14][CH2:13][O:12][N:11]=2)[C:4]([S:8][CH3:9])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 108783423-(2-Methyl-6-methylthiophenyl)-4,5-dihydroisoxazole

Product 1

HCID 9860657Isoxazole, 3-[3-bromo-2-methyl-6-(methylthio)phenyl]-4,5-dihydro-

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

At 0° C., 10 g (48 mmol) of 3-(2-methyl-6-methylthiophenyl)-4,5-dihydroisoxazole are added a little at a time to 120 ml of conc. sulfuric acid, and the mixture is stirred for approximately 30 minutes. 3.7 g (23 mmol) of bromine are then added dropwise, and the mixture is stirred at 0° C. for 2.5 hours. Over a period of approximately 45 minutes, the mixture is subsequently allowed to warm to room temperature. A homogeneous solution forms. For work-up, the reaction mixture is poured into ice-water and extracted three times with methylene chloride. The organic phase is washed with sodium bicarbonate solution, dried with magnesium sulfate and concentrated. This gives 11.4 g of crude product which is employed in the next step without any further purification.

Workup

  1. stirringthe mixture is stirred at 0° C. for 2.5 hours
  2. waitOver a period of approximately 45 minutes
  3. extractionextracted three times with methylene chloride
  4. washThe organic phase is washed with sodium bicarbonate solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customThis gives 11.4 g of crude product which is employed in the next step without any further purification

Sources & evidence

ORD record
ord-253d125705d747e7a25dce149bec5f7f
Source dataset
uspto-grants-2004_03
Patent number
US06706886B2

Reaction notes

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