Hydrogen Bromide → Codeinone

HRID 1390814Notes

Reaction equation

HRID 1390814 reaction equation
Br.[CH3:2][N:3]1[C@@H:19]2[CH2:20][C:8]3[CH:9]=[CH:10][C:11]([O:23][CH3:24])=[C:12]4[O:13][C@H:14]5[C:15]([O:21]C)=[CH:16][CH:17]=[C:18]2[C@:6]5([C:7]=34)[CH2:5][CH2:4]1.C(=O)=O>C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:2][N:3]1[C@@H:19]2[CH2:20][C:8]3[CH:9]=[CH:10][C:11]([O:23][CH3:24])=[C:12]4[O:13][C@H:14]5[C:15]([CH:16]=[CH:17][C@@H:18]2[C@:6]5([C:7]=34)[CH2:5][CH2:4]1)=[O:21]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 280Carbon DioxideHCID 5324289Thebaine

Product 1

HCID 5459910Codeinone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

Anhydrous hydrogen bromide in glacial acetic acid (6 ml of 45% w/v solution) was added dropwise with stirring to a cooled (-15° C.) solution of thebaine (2 g) in chloroform (6 ml) over a period of 9 minutes. When the addition was complete the Drikold bath was removed and the temperature allowed to rise.

Workup

  1. additionWhen the addition
  2. customwas removed

Sources & evidence

ORD record
ord-91379730c94043939784645b16d71596
Source dataset
uspto-grants-1979_02
Patent number
US04140687

Reaction notes

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