Diethyl Ether → 2-bromo-1-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]ethanone hydrochloride

HRID 1517183Notes

Reaction equation

HRID 1517183 reaction equation
[ClH:1].[CH2:2]([N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15](=[O:17])[CH3:16])=[CH:14][C:9]=2[N:8]=[C:7]1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)[CH:3]([CH3:5])[CH3:4].[Br:26]Br.C(OCC)C>C(O)(=O)C>[ClH:1].[Br:26][CH2:16][C:15]([C:13]1[CH:12]=[CH:11][C:10]2[N:6]([CH2:2][CH:3]([CH3:4])[CH3:5])[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)=[N:8][C:9]=2[CH:14]=1)=[O:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 686437671-[1-Isobutyl-2-(3-methoxy phenyl)-1h-benzimidazol-5-yl]ethanone hydrochloride

Product 1

HCID 866472782-bromo-1-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]ethanone hydrochlorideYield 63.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 32.7 g (91.3 mM) of 1-[1-isobutyl-2-(3-methoxy phenyl)-1H-benzimidazol-5-yl]ethanone hydrochloride in 330 ml of acetic acid are added dropwise 4.7 ml (91.4 mM) of bromine. 100 ml of diethyl ether are then added and the crystalline product is filtered off. It is washed with diethyl ether and dried under vacuum to give 35 g of 2-bromo-1-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]ethanone hydrochloride.

Workup

  1. filtrationthe crystalline product is filtered off
  2. washIt is washed with diethyl ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-c0d94855e69047cdbc0ae5ed2fe9cd33
Source dataset
uspto-grants-2012_07
Patent number
US08232272B2

Reaction notes

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