1,3-Dibromo-5,5-dimethylhydantoin → 2-Bromomethylnaphthalene

HRID 1427168Notes

Reaction equation

HRID 1427168 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[Br:12]N1C(C)(C)C(=O)N(Br)C1=O>C(OCC)(=O)C>[Br:12][CH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 70552-Methylnaphthalene

Product 1

HCID 703202-BromomethylnaphthaleneYield 91.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Under nitrogen gas flow, 600 g of 2-methylnaphthalene was dissolved into 6,000 ml of ethyl acetate, the mixture was then added with 422 g of 1,3-dibromo-5,5-dimethylhydantoin, and heated to 40° C. The mixture was added with 7.4 g of V-65 from Wako Pure Chemical Industries, Ltd., and allowed to react at 40° C. for 7 hours. Thereafter, the reaction liquid was allowed to react at 65° C. for 3 hours, and then cooled. The reaction liquid was successively washed with aqueous sodium hydrogen carbonate solution and distilled water, and then concentrated. The concentrate was added with 3,600 ml of isopropanol, stirred for 30 minutes, added with 900 ml of distilled water, and further stirred for 30 minutes. Precipitated solid was collected by filtration, added with 1,800 ml of isopropanol, the mixture was stirred for 30 minutes, added with 450 ml of distilled water, and further stirred for 30 minutes. The resultant solid was collected by filtration, and dried, to thereby obtain 300 g of 2-bromomethylnaphthalene.

Workup

  1. additionThe mixture was added with 7.4 g of V-65 from Wako Pure Chemical Industries, Ltd
  2. customto react at 40° C. for 7 hours
  3. customThereafter, the reaction liquid
  4. customto react at 65° C. for 3 hours
  5. temperaturecooled
  6. customThe reaction liquid
  7. washwas successively washed with aqueous sodium hydrogen carbonate solution
  8. distillationdistilled water
  9. concentrationconcentrated
  10. additionThe concentrate was added with 3,600 ml of isopropanol
  11. additionadded with 900 ml of distilled water
  12. stirringfurther stirred for 30 minutes
  13. customPrecipitated solid
  14. filtrationwas collected by filtration
  15. additionadded with 1,800 ml of isopropanol
  16. stirringthe mixture was stirred for 30 minutes
  17. additionadded with 450 ml of distilled water
  18. stirringfurther stirred for 30 minutes
  19. filtrationThe resultant solid was collected by filtration
  20. customdried

Sources & evidence

ORD record
ord-85fd36d850de4b3d98cce8ff0a786a05
Source dataset
uspto-grants-2015_01
Patent number
US08933144B2

Reaction notes

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