Bromine → HCID 19845921, compound

HRID 2309137Notes

Reaction equation

HRID 2309137 reaction equation
[NH:1]1[C:8]2=[CH:9][CH:10]=[CH:11][CH2:12][CH:7]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:13].P(Cl)(Cl)(Cl)(Cl)Cl.[Br:20]Br>C(Cl)(Cl)Cl.II>[Br:20][CH:3]1[CH2:4][CH2:5][CH2:6][CH:7]2[CH2:12][CH:11]=[CH:10][CH:9]=[C:8]2[NH:1][C:2]1=[O:13]

Participants

6

Reactant 3

HCID 24408BromineHCID 24819Phosphorus pentachlorideHCID 19845916HCID 19845916, compound

Product 1

HCID 19845921HCID 19845921, compound

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 6212ChloroformSolvent2×

Procedure

To a solution of 15 gm (0.084 mol) of hexahydrobenzoazocin-2-one (Chemica Scandinavia, 18, 191 (1964)) in 150 ml of chloroform at 0° C. was added 8.8 gm of PCl5 in small increments over a period of an hour. To this reaction mixture was added 70 mg of iodine, followed by the slow dropwise addition of 84 ml of a 1M solution of bromine in chloroform and this reaction mixture was warmed to room temperature and stirred for 1 hour, at which time it was concentrated at reduced pressure. A mixture of ice and water was added to the crude product and the mixture was extracted three times with methylene chloride. The combined organic fractions were filtered through MgSO4 and concentrated at reduced pressure. The solid bromide was recrystallized with a mixture of chloroform and hexanes to give 12 gm of pure 3-bromohexahydrobenzoazocin-2-one.

Workup

  1. concentrationwas concentrated at reduced pressure
  2. additionA mixture of ice and water
  3. additionwas added to the crude product
  4. extractionthe mixture was extracted three times with methylene chloride
  5. filtrationThe combined organic fractions were filtered through MgSO4
  6. concentrationconcentrated at reduced pressure
  7. customThe solid bromide was recrystallized with a mixture of chloroform and hexanes

Sources & evidence

ORD record
ord-5a021b71d2414fec9a27e7f136fcada6
Source dataset
uspto-grants-1987_09
Patent number
US04692522

Reaction notes

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