Hydrogen Bromide → 5-Bromoazepan-4-one hydrobromide

HRID 400418Notes

Reaction equation

HRID 400418 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-898c5562c50444c1be12e960d00e6f21
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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