Bromine → HCID 53700356, compound

HRID 840103Notes

Reaction equation

HRID 840103 reaction equation
[O:1]1[CH:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH2:10][CH2:11][CH:12]2[OH:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[CH:3][CH:4]=[CH:5]2.[Br:21]Br>C(O)(=O)C>[Br:21][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:18]([CH3:19])[CH2:17][CH2:16][C@:14]45[C:15]=2[C:2]=1[O:1][CH:13]4[CH:12]([OH:20])[CH2:11][CH2:10][C@@H:9]35

Participants

4

Reactant 2

HCID 24408BromineHCID 54153354HCID 54153354, compound

Product 1

HCID 53700356HCID 53700356, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3.1 g (11.4 mmol) of 4,5-epoxy-17-methylmorphinan-6-ol were dissolved in 150 ml of glacial acetic acid and 11.4 ml of a 1M solution of Br2 in AcOH were added dropwise. After 1 h, AcOH was removed in vacuo, the residue was taken up with water, the aqueous solution was brought to pH 7 with a saturated NAHCO3 solution and extracted with AcOEt. The organic phase was dried over NA2SO4, the solvent was removed in vacuo, yielding 3.6 g of the title product.

Workup

  1. customAcOH was removed in vacuo
  2. extractionextracted with AcOEt
  3. customThe organic phase was dried over NA2SO4
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2874b640c1034cfb9a6944a3940a2bc5
Source dataset
uspto-grants-2002_04
Patent number
US06365594B1

Reaction notes

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