Carbon Tetrachloride → tert-Butyl 4-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate

HRID 1352013Notes

Reaction equation

HRID 1352013 reaction equation
[CH3:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl>>[Br:18][CH2:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 15744963t-butyl 4-methyl-1H-benzimidazole-1-carboxylate

Product 1

HCID 15744964tert-Butyl 4-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylateYield 42.4%

Procedure

A mixture of 4-methylbenzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester (6.50 g, 28.0 mmol) and N-bromosuccinimide (5.50 g, 30.9 mmol) in carbon tetrachloride (75 mmol) was stirred and irradiated with a 250 W flood lamp for 1 h. The reaction mixture was allowed to cool and the solid was filtered off and discarded. The filtrate was evaporated and purified by HPLC (20% ethyl acetate/hexanes) to give 4-(bromomethyl)benzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester (3.69 g, 42%).

Workup

  1. customirradiated with a 250 W flood lamp for 1 h
  2. temperatureto cool
  3. filtrationthe solid was filtered off
  4. customThe filtrate was evaporated
  5. custompurified by HPLC (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9a28564e9afe4838938692bab49bfad9
Source dataset
uspto-grants-2007_05
Patent number
US07217728B2

Reaction notes

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