Sulfuric Acid → HCID 13854569, compound

HRID 1193474Notes

Reaction equation

HRID 1193474 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]12[CH2:15][CH:12]([CH2:13][CH2:14]1)[C:11]1[CH:16]=[CH:17][CH:18]=[CH:19][C:10]2=1.S(=O)(=O)(O)O>O>[Br:1][CH:14]1[CH:9]2[CH2:15][CH:12]([C:11]3[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=32)[CH2:13]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 1382721,2,3,4-Tetrahydro-1,4-methanonaphthalene2×

Product 1

HCID 13854569HCID 13854569, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 g of N-bromosuccinimide are added in small portions over approximately two hours to a mixture of 5 g of benzonorbornene, stirred into 10 cm3 of water and 10 cm3 of sulphuric acid and heated to a temperature between 50° C. and 55° C. The progress of the reaction is followed by gas phase chromatography. When the benzonorbornene has been completely converted, the reaction mixture, at room temperature, is extracted with methylene chloride. The organic phase is washed with sodium bicarbonate until the pH of the washings is neutral and is then dried over magnesium sulphate and concentrated. 7 g of crude 2-bromobenzonorbornene are obtained and purified by distillation under reduced pressure. After distillation, 4 g of pure product are obtained. This product is a light-yellow liquid whose boiling point is 70°-75° C. at a pressure of approximately 2.65 10-5 bar. Its proton nuclear magnetic resonance spectrum corresponds to the 2-bromobenzonorbornene structure.

Workup

  1. temperatureheated to a temperature between 50° C. and 55° C
  2. extractionthe reaction mixture, at room temperature, is extracted with methylene chloride
  3. washThe organic phase is washed with sodium bicarbonate until the pH of the washings
  4. dry with materialis then dried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c222f22311a64437b7adfbab331ec582
Source dataset
uspto-grants-1989_03
Patent number
US04810694

Reaction notes

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