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CAS No. : | 132873-77-9 | MDL No. : | MFCD13182538 |
Formula : | C13H15BrN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RJQPRKXEVWZMAO-UHFFFAOYSA-N |
M.W : | 311.17 | Pubchem ID : | 15744964 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501 | UN#: | 3261 |
Hazard Statements: | H302-H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With phosphorus tribromide In diethyl ether; dichloromethane at 0 - 20℃; for 2.08333 h; Inert atmosphere | Intermediate AG: 4-Bromomethyl-benzoimidazole-1-carboxylic acid tert-butyl esterTo a solution of 4-Hydroxymethyl-benzoimidazole-1 -carboxylic acid tert-butyl ester (Step AG1 , 330 mg, 1 .329 mmol) in Et20 (5 ml) at 0 °C under Ar was added PBr3 (1 M in CH2CI2) (1.462 ml, 1.462 mmol), dropwise, causing a thick precipitation. After 5 minutes at 0 °C, the medium was allowed to reach rt. After 1 h at rt, PBr3 (1 M in CH2CI2) (0.133 ml, 0.133 mmol) was added under stirring, followed by CH2CI2 (2 ml). After a further 1 h at rt, the medium was carefully quenched with saturated sodium bicarbonate solution (20 ml, strong C02 evolution) and extracted with EtOAc (3 x 15 ml). Drying of the combined organics over Na2S04 and concentration afforded a clear oil. The oil was purified by chromatography on silica gel, using a 0percent to 100percent gradient of eluent B (EtOAc/ CH2CI2 / heptane: 1/2/2) in eluent A (heptane/ CH2CI2 : 1/1 ), yielding the title product as a colorless oil, 153 mg (37percent). HPLC/MS (Method A) tR1.70 minute, M+H 310.9-312.9 . 1 H NMR (DMSO-d6) Ppm 1 .69 (s, 9 H) 4.95 (s, 2 H) 7.38 (m, 2 H) 7.94 (d, 1 H) 8.49 (s, 1 H). |
37% | With phosphorus tribromide; sodium hydrogencarbonate In diethyl ether; dichloromethane at 0 - 20℃; for 2.08333 h; Argon atmosphere | Intermediate AG: 4-Bromomethyl-benzoimidazole-1-carboxylic acid tert-butyl esterTo a solution of 4-Hydroxymethyl-benzoimidazole-1 -carboxylic acid tert-butyl ester (Step AG1 , 330 mg, 1 .329 mmol) in Et20 (5 ml) at 0 °C under Ar was added PBr3 (1 M in CH2CI2) (1.462 ml, 1.462 mmol), dropwise, causing a thick precipitation. After 5 minutes at 0 °C, the medium was allowed to reach rt. After 1 h at rt, PBr3 (1 M in CH2CI2) (0.133 ml, 0.133 mmol) was added under stirring, followed by CH2CI2 (2 ml). After a further 1 h at rt, the medium was carefully quenched with saturated sodium bicarbonate solution (20 ml, strong C02 evolution) and extracted with EtOAc (3 x 15 ml). Drying of the combined organics over Na2S04 and concentration afforded a clear oil. The oil was purified by chromatography on silica gel, using a 0percent to 100percent gradient of eluent B (EtOAc/ CH2CI2 / heptane: 1/2/2) in eluent A (heptane/ CH2CI2 : 1/1 ), yielding the title product as a colorless oil, 153 mg (37percent). HPLC/MS (Method A) tR1.70 minute, M+H 310.9-312.9 . 1 H NMR (DMSO-d6) Ppm 1 .69 (s, 9 H) 4.95 (s, 2 H) 7.38 (m, 2 H) 7.94 (d, 1 H) 8.49 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With N-Bromosuccinimide In tetrachloromethane | C. 4-(Bromomethyl)benzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester 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 (20percent ethyl acetate/hexanes) to give 4-(bromomethyl)benzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester (3.69 g, 42percent). |
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