Hydrogen Bromide → 5-Bromoazepan-4-one hydrobromide

HRID 239095Notes

Reaction equation

HRID 239095 reaction equation
[BrH:1].Cl.[NH:3]1[CH2:9][CH2:8][CH2:7][C:6](=[O:10])[CH2:5][CH2:4]1.BrBr>C(O)(=O)C>[BrH:1].[Br:1][CH:7]1[CH2:8][CH2:9][NH:3][CH2:4][CH2:5][C:6]1=[O:10]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 22021728Azepan-4-one hydrochloride

Product 1

HCID 226207665-Bromoazepan-4-one hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

32 mL 62% HBr solution in 50 mL conc. acetic acid was added to 50 g hexahydro-azepin-4-on hydrochloride in 600 mL conc. acetic acid. Then 17.2 mL bromine in 50 mL conc. acetic acid was dropped to the reaction. The solvent was removed and the residue was crystallized from a mixture of DCM/MeOH (8/2) to give 79 g of the desired compound.

Workup

  1. customThe solvent was removed
  2. customthe residue was crystallized from a mixture of DCM/MeOH (8/2)

Sources & evidence

ORD record
ord-4fc4ac996c1e4153b2ceec3fc966df9f
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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