Hydrogen Bromide → HCID 18663584, compound

HRID 1956572Notes

Reaction equation

HRID 1956572 reaction equation
[Cl:1][C:2]1[C:12]2[CH:11]=[C:10]([CH2:13]O)[C:9]3[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=3[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.O.[BrH:20]>>[Br:20][CH2:13][C:10]1[C:9]2[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=2[O:7][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:12]=2[CH:11]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 18663597HCID 18663597, compound

Product 1

HCID 18663584HCID 18663584, compoundYield 38.7%

Procedure

4.58 g (17.70 mmol) of (1-chlorodibenz[b,f]oxepin-10-yl)-methanol are heated under reflux in 50 ml of 48% hydrobromic acid for 2 hours. The mixture is cooled, water is added and the mixture is extracted 3× with ethyl acetate. The organic phases are washed with brine, dried over sodium sulfate and concentrated. 5.57 g of crude product are obtained which becomes solid on being left to stand (3 days). Recrystallisation from tert-butyl methyl ether/hexane yields 2.205 g (6.86 mmol)=38.7% of 10-bromomethyl-1-chloro-dibenz[b,f]oxepine in the form of light-beige crystals; TLC (silica gel; ethyl acetate; UV): Rf =0.73; 1H-NMR (CDCl3, 200 MHz): 4.60 (s, 2H); 7.15-7.58 (m, 8H).

Workup

  1. temperatureThe mixture is cooled
  2. extractionthe mixture is extracted 3× with ethyl acetate
  3. washThe organic phases are washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custom5.57 g of crude product are obtained which
  7. waiton being left
  8. custom(3 days)
  9. customRecrystallisation from tert-butyl methyl ether/hexane

Sources & evidence

ORD record
ord-34fae7d5d85440309c97e430888c7337
Source dataset
uspto-grants-1998_07
Patent number
US05780500

Reaction notes

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