Hydrogen Bromide → 5-Bromoazepan-4-one hydrobromide

HRID 1019637Notes

Reaction equation

HRID 1019637 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 AcidSolvent2×

Procedure

27 mL 33% HBr solution was added to 20 g hexahydro-azepin-4-one hydrochloride in 225 mL conc. acetic acid. Subsequently 6.9 mL bromine in 25 mL conc. acetic acid was added dropwise to the reaction mixture and the mixture was stirred 30 min at RT. The solvent was removed and the residue was crystallized with acetonitrile to give 27.9 g of the desired compound.

Workup

  1. customThe solvent was removed
  2. customthe residue was crystallized with acetonitrile

Sources & evidence

ORD record
ord-aa5065167db54a449db3ced1f744659a
Source dataset
uspto-grants-2014_05
Patent number
US08716277B2

Reaction notes

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