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Chemical Structure| 4857-06-1 Chemical Structure| 4857-06-1
Chemical Structure| 4857-06-1

2-Chlorobenzimidazole

CAS No.: 4857-06-1

4.5 *For Research Use Only !

Cat. No.: A292813 Purity: 97%

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Product Details of 2-Chlorobenzimidazole

CAS No. :4857-06-1
Formula : C7H5ClN2
M.W : 152.58
SMILES Code : ClC1=NC2=CC=CC=C2N1
MDL No. :MFCD00051944
InChI Key :AYPSHJCKSDNETA-UHFFFAOYSA-N
Pubchem ID :78572

Safety of 2-Chlorobenzimidazole

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501

Application In Synthesis of 2-Chlorobenzimidazole

* 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.

  • Downstream synthetic route of [ 4857-06-1 ]

[ 4857-06-1 ] Synthesis Path-Downstream   1~20

  • 1
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  • [ 506-59-2 ]
  • [ 2851-13-0 ]
  • 2
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  • [ 124-40-3 ]
  • [ 2851-13-0 ]
YieldReaction ConditionsOperation in experiment
89% In water; N,N-dimethyl-formamide; at 200℃; for 0.5h; Commercially available 2-chloro-1H-benzo[d]imidazole (250 mg, 1.64 mmol) was dissolved in DMF (4.7 mL), dimethylamine (50% aqueous solution, 0.50 mL, 4.92 mmol) was added, and the mixture was stirred with heating at 200C for 30 min in an Emrys Optimizer microwave synthesizer. Water was added to the mixture, and the precipitated crystals were collected by suction filtration to give N,N-dimethyl-1H-benzo[d]imidazole-2-amine (234 mg, 89%). ESIMS m/z: 162 (M + H)+; 1H NMR (270 MHz, DMSO-d6, delta): 3.03 (s, 6H), 6.79-6.97 (m, 2H), 7.07-7.20 (m, 2H), 11.17 (br s, 1H)
  • 4
  • [ 4857-06-1 ]
  • [ 352-11-4 ]
  • [ 84946-20-3 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; Step B: 2-chloro 1-(4 fluorobenzyl) benzimidazole 11 g 2-chlorobenzimidazole are dissolved in 74 ml water and 17.35 ml 30% sodium hydroxide. The mixture is heated to 82 C. and to this they are slowly added 23.76 g 4-fluorobenzyl chloride within 5 hours. When the reaction is achieved, the solution is cooled to 20 C. and extracted with methylene chloride. The compound is recrystallized from ethyl acetate.
With potassium iodide; sodium carbonate; In chloroform; N,N-dimethyl-formamide; EXAMPLE 8 A mixture of 60 parts of 2-chloro-1H-benzimidazole, 58 parts of 1-(chloromethyl)-4-fluorobenzene, 42.5 parts of sodium carbonate, 0.1 parts of potassium iodide and 135 parts of N,N-dimethylformamide was stirred and heated overnight at 70 C. The reaction mixture was poured into water. The precipitated product was filtered off and dissolved in trichloromethane. The solution was dried, filtered and evaporated. The residue was crystallized from 2,2'-oxybispropane, yielding 62.5 parts of 2-chloro-1-(4-fluorophenylmethyl)-1H-benzimidazole (61).
  • 5
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  • [ 459-46-1 ]
  • [ 84946-20-3 ]
YieldReaction ConditionsOperation in experiment
91.1% To a solution of 2-chlorobenzomethylene (5 g, 32.7 mmol) was added 30 ml of acetonitrile and potassium hydroxide (2.62 g, 46.6 mmol) Heated to 80 C, stirred for 30min, the solution clarified; after cooling to room temperature, adding bromine bromide (9.29g, 49.1 mmol) 80 C reflux 5h, the reaction solution was white turbid; the reaction solution with dichloromethane extraction three times (100mLX3), distilled water The organic layers were combined, dried over anhydrous magnesium sulfate, suction filtered and concentrated to give a white solid which was recrystallized from acetone / petroleum ether and cooled And filtered, dried to give a white solid in a yield of 91.1%.
77% 2-Chloro-1 H- benzimidazoie (13.12 mmoi, 2 g), KOH (18.37 mmol, 1 .03 g) and dry acetonitrile (80 mL) was heated to reflux and stirred for 1 hour, 4-fluorobenzyl bromide (19.68 mmol, 2.45 mL) was added. The reaction mixture was refluxed while stirring for 6 hours. The reaction mixture was cooled to room temperature, washed with water, and extracted with dichloromethane. The organic layer was evaporated and recrystallized with dichloromethane and hexane to afford Compound 2 (2,6 g, 77%) as a white solid. [00122] NMR (500 MHz, Acetone-d6) δ 7.68 -7.59 (m, 1 H), 7.58 -7.50 (m, 1 H), 7.39 -7.30 (m, 2H), 7.31-7.23 (m, 2H), 7.19 - 7.07 (m, 2H), 5.55 (d, J = 1.1 Hz, 2H). 13C NMR (126 MHz, cd3od) δ 163.87 (d, J = 245.6 Hz), 142.30, 141.86, 136.22, 132.89, 130.17, 130.11 , 124.93, 124.39, 1 19.58, 1 16.85, 1 16.67, 11 1.66, 48.04. IR (neat): 1602, 1506, 1233 cm- 1 , m/z: [(M+H)+] calcd for (C14H1 1CIFN2+) 261 .0595; Found 261 .0599. mp 70-74 C.
77% 2-Chloro-1 H- benzimidazoie (13.12 mmoi, 2 g), KOH (18.37 mmol, 1 .03 g) and dry acetonitrile (80 mL) was heated to reflux and stirred for 1 hour, 4-fluorobenzyl bromide (19.68 mmol, 2.45 mL) was added. The reaction mixture was refluxed while stirring for 6 hours. The reaction mixture was cooled to room temperature, washed with water, and extracted with dichloromethane. The organic layer was evaporated and recrystallized with dichloromethane and hexane to afford Compound 2 (2,6 g, 77%) as a white solid. [00122] NMR (500 MHz, Acetone-d6) δ 7.68 -7.59 (m, 1 H), 7.58 -7.50 (m, 1 H), 7.39 -7.30 (m, 2H), 7.31-7.23 (m, 2H), 7.19 - 7.07 (m, 2H), 5.55 (d, J = 1.1 Hz, 2H). 13C NMR (126 MHz, cd3od) δ 163.87 (d, J = 245.6 Hz), 142.30, 141.86, 136.22, 132.89, 130.17, 130.11 , 124.93, 124.39, 1 19.58, 1 16.85, 1 16.67, 11 1.66, 48.04. IR (neat): 1602, 1506, 1233 cm- 1 , m/z: [(M+H)+] calcd for (C14H1 1CIFN2+) 261 .0595; Found 261 .0599. mp 70-74 C.
With sodium hydroxide; In N-methyl-acetamide; hexane; dichloromethane; water monomer; PREPARATION 2 (1-(4-Fluorobenzyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine Combine 2-chloro-1H-benzimidazole (17.75 g, 116 mmol) and 4-fluorobenzyl bromide (26.6 g, 141 mmol) in dimethylformamide (100 mL). Add a solution of sodium hydroxide (50 g) in water (75 mL). (Caution, exothermic). After 30 minutes, pour the reaction mixture into water (1800 mL) and stir to form a solid. After 1 hour, collect the solid by filtration, dissolve the solid in dichloromethane, and extract with water. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on a short column of silica gel eluding with 5% ethyl acetate/dichloromethane to give a solid. Recrystallize from chloroform/hexane to give, after drying, 1-(4-fluorobenzyl)-2-chloro-1H-benzimidazole.
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 110℃; for 12h; General procedure: Alternatively, to a stirred mixture of 2-chlorobenzimidazole (1.0 eq.) and R3CH2Br (1.0 eq.) in dimethylformamide was added N,N-diisopropylethylamine (1.5 eq.). The reaction mixture was heated to 110 C and stirred for 12 h. After the reaction was completed, the reaction mixture was cooled down to room temperature, diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (ethyl acetate/hexane) to give desired product 1d.
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 110℃; for 12h; General procedure: To a stirred solution of 1c (1.0 eq.) and POCl3 (10 eq.) was addeda few drops of conc. HCl. The reaction mixture was heated to 150 C and stirred for 3 h. After the reaction was completed, the reaction mixture was poured into ice water, neutralized with 1 N aq. NaOH and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4 and concentrated in vacuo to givecrude product 1d. Alternatively, to a stirred mixture of 2-chlorobenzimidazole (1.0 eq.) and R3CH2Br (1.0 eq.) in dimethylformamide was added N,N-diisopropylethylamine (1.5 eq.). The reaction mixture was heated to 110 C and stirred for 12 h. After the reaction was completed, the reaction mixture was cooled down to room temperature, diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (ethyl acetate/hexane) to give desired product 1d.
General procedure: In a round bottom flask fitted with amagnetic stirrer, 2-chloro-1H-benzimidazole, 3, (0.50 g, 3.3 mmol) was dissolved in DMSO (3mL) and then NaH (60%; 0.19 g, 4.9 mmol) was added at 0 C and stirred for 1h. Next, benzylbromide (0.67 g, 3.9 mmol) was added to the suspension and the reaction was stirred at rt for 12h. Ice-cold water (15 mL) was added to the mixture and resulting precipitate was collected viafiltration. The filtrate was washed with water and dried under vacuum to give desired product, 4,as a white solid (0.75 g, 88%). LCMS: RT = 2.69 min., >98% 215 and 254 nm, m/z = 243.0 [M+ H]+. 1H NMR (499 MHz, CDCl3) δ 7.68 (d, J = 7.4 Hz, 1H), 7.35 - 7.24 (m, 5H), 7.16 (d, J =6.8 Hz, 2H), 5.38 (s, 2H). 13C NMR (126 MHz, CDCl3) δ 141.33, 134.83, 128.99, 128.22, 126.76,123.53, 123.05, 119.18, 109.98, 47.94.
With sodium hydroxide; In N-methyl-acetamide; hexane; dichloromethane; water monomer; PREPARATION 5 Synthesis of (1-(4-fluorobenzyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine Combine 2-chloro-1H-benzimidazole (17.75 g, 116 mmol) and 4-fluorobenzyl bromide (26.6 g, 141 mmol) in dimethylformamide (100 mL). Add a solution of sodium hydroxide (50 g) in water (75 mL). (Caution, exothermic). After 30 minutes, pour the reaction mixture into water (1800 mL) and stir to form a solid. After 1 hour, collect the solid by filtration, dissolve the solid in dichloromethane, and extract with water. Dry the organic layer over Na2 SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on a short column of silica gel eluding with 5% ethyl acetate/dichloromethane to give a solid. Recrystallize from chloroform/hexane to give, after drying, 1-(4-fluorobenzyl)-2-chloro-1H-benzimidazole.

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  • ethyl halide [ No CAS ]
  • [ 58533-15-6 ]
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  • p-FC6H4CH2X [ No CAS ]
  • [ 84946-20-3 ]
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  • [ 24424-99-5 ]
  • [ 214147-60-1 ]
YieldReaction ConditionsOperation in experiment
With dmap; In acetonitrile; Preparation 46 tert-Butyl 2-chloro-1H-1,3-benzimidazole-1-carboxylate 2-Chloro-1H-1,3-benzimidazole (1.07 g) was added to a solution of di-tert-butyldicarbonate (1.83 g) and 4-dimethylaminopyridine (86 mg) in acetonitrile (15 ml). The reaction mixture was stirred at room temperature for 30 minutes, after which time the solvent was removed under reduced pressure. The crude product was then purified by column chromatography on silica gel eluding with a solvent gradient of 100:0 changing to 90:10, by volume, hexane:ethyl acetate to afford tert-butyl 2-chloro-1H-1,3-benzimidazole-1-carboxylate (1.68 g) as a white solid. 1H-NMR (CDCl3) delta: 7.90 (1H, m), 7.35 (1H, m), 7.40 (2H, m), 1.80 (9H, s). MS: 253 (MH+).
With triethylamine; In isopropyl alcohol; at 20℃; for 19.0h;Product distribution / selectivity; Example 1. 4- (2- ( (2, 6-Dimethylphenyl) oxy)-1H-benzimidazol-1-yl)-N- (4- (4- methyl-l-piperazinyl) phenyl)-2-pyrimidinamine; Step A: 2-Chloro-benzoimidazole-l-carboxylic acid tert-butyl ester; Di-tert-butyldicarbonate (12.270 g, 56.221 mmol) was added to a solution of 2- chlorobenzimidazole (8. 41 g, 55.119 mmol) and triethylamine (20 mL) in isopropanol (90 mL). The reaction mixture was stirred at room temperature for 19 h and then concentrated. The resulting material was purified via column chromatography on silica gel (eluting with dichloromethane) to afford 2-chloro- benzoimidazole-1-carboxylic acid tert-butyl ester as a white solid.
  • 9
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  • [ 51498-33-0 ]
  • cis 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In ethanol; ethyl acetate; A mixture of 2-Chlorobenzimidazole (I) (0.9 g, 5.9 mmol) and ethyl-4-amino-cyclohexane carboxylate (1.1 g, 5.4 mmol) were placed in a glass high pressure tube. Diisopropylethylamine (2.8 mL, 16.2 mmol) was added, the reaction vessel was sealed and heated to 200 C. for 4 h and allowed to cool to room temperature. Next was added 5 mL EtOH and heated to dissolve the reaction mixture. The reaction mixture was partitioned between aqueous NaHCO3 and EtOAc, and the organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated. Purification of the crude product on silica gel (gradient, 1:1 hexanes:EtOAc to EtOAc) gave the cis 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (J) (0.5 g) and the trans 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (K) (0.5 g). Data for (J): 1H NMR (300 MHz, CDCl3) delta 7.28 (br s, 2 H), 7.02 (m, 2 H), 5.16 (br s, 1 H), 4.15 (q, 2 H), 3.97 (br s, 1 H), 2.40 (br s, 1 H), 1.80-1.54 (m, 8 H), 1.22 (t, 3 H); mass spectrum m/z 288 [(M+H)+; calcd for C16H22N3O2: 288].
With N-ethyl-N,N-diisopropylamine; In ethanol; ethyl acetate; A mixture of 2-Chlorobenzimidazole (I) (0.9 g, 5.9 mmol) and ethyl-4-amino-cyclohexane carboxylate (1.1 g, 5.4 mmol) were placed in a glass high pressure tube. Diisopropylethylamine (2.8 mL, 16.2 mmol) was added, the reaction vessel was sealed and heated to 200 C. for 4 h and allowed to cool to room temperature. Next was added 5 mL EtOH and heated to dissolve the reaction mixture. The reaction mixture was partitioned between aqueous NaHCO3 and EtOAc, and the organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated. Purification of the crude product on silica gel (gradient, 1:1 hexanes:EtOAc to EtOAc) gave the cis 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (J) (0.5 g) and the trans 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (K) (0.5 g). Data for (J): 1H NMR (300 MHz, CDCl3) delta7.28 (br s, 2 H), 7.02 (m, 2 H), 5.16 (br s, 1 H), 4.15 (q, 2 H), 3.97 (br s, 1 H), 2.40 (br s, 1 H), 1.80-1.54 (m, 8 H), 1.22 (t, 3 H); mass spectrum m/z 288 [(M+H)+; calcd for C16H22N3O2: 288].
With N-ethyl-N,N-diisopropylamine; In ethanol; ethyl acetate; A mixture of 2-Chlorobenzimidazole (I) (0.9 g, 5.9 mmol) and ethyl-4-amino-cyclohexane carboxylate (1.1 g, 5.4 mmol) were placed in a glass high pressure a tube. Diisopropylethylamine (2.8 mL, 16.2 mmol) was added, the reaction vessel was sealed and heated to 200 C. for 4 h and allowed to cool to room temperature. Next was added 5 mL EtOH and heated to dissolve the reaction mixture. The reaction mixture was partitioned between aqueous NaHCO3 and EtOAc, and the organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated. Purification of the crude product on silica gel (gradient, 1:1 hexanes:EtOAc to EtOAc) gave the cis 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (J) (0.5 g) and the trans 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (K) (0.5 g) Data for (J): 1H NMR (300 MHz, CDCl3) delta 7.28 (br s, 2H), 7.02 (m, 2H), 5.16 (br s, 1H), 4.15 (q, 2H), 3.97 (br s, 1H), 2.40 (br s, 1H), 1.80-1.54 (m, 8H), 1.22 (t, 3H); mass spectrum m/z 288 [(M+H)+; calcd for C16H22N3O2: 288].
  • 10
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  • [ 51498-33-0 ]
  • cis 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester [ No CAS ]
  • trans 4-(1H-benzirnidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In ethanol; ethyl acetate; A mixture of 2-Chlorobenzimidazole (I) (0.9 g, 5.9 mmol) and ethyl-4-amino-cyclohexane carboxylate (1.1 g, 5.4 mmol) were placed in a glass high pressure tube. Diisopropylethylamine (2.8 mL, 16.2 mmol) was added, the reaction vessel was sealed and heated to 200 C. for 4 h and allowed to cool to room temperature. Next was added 5 mL EtOH and heated to dissolve the reaction mixture. The reaction mixture was partitioned between aqueous NaHCO3 and EtOAc, and the organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated. Purification of the crude product on silica gel (gradient, 1:1 hexanes:EtOAc to EtOAc) gave the cis 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (J) (0.5 g) and the trans 4-(1H-benzirnidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (K) (0.5 g). Data for (J): 1H NMR (300 MHz, CDCl3) delta 7.28 (br s, 2 H), 7.02 (m, 2 H), 5.16 (br s, 1 H), 4.15 (q, 2 H), 3.97 (br s, 1 H), 2.40 (br s, 1 H), 1.80-1.54 (m, 8 H), 1.22 (t, 3 H); mass spectrum m/z 288 [(M+H)+; calcd for C16H22N3O2: 288].
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  • [ 75-03-6 ]
  • [ 58533-15-6 ]
YieldReaction ConditionsOperation in experiment
10.0 g (61%) With NaH; In N,N-dimethyl-formamide; mineral oil; Step 1) Preparation of 2-Chloro-1-ethylbenzimidazole To a cooled (0 C.) stirred suspension of NaH (60% dispersion in mineral oil; 7.08 g, 0.118 mol) in DMF (100 mL) was added 2-chlorobenzimidazole (15.00 g, 0.098 mol). The mixture was warmed to room temperature and stirred for 1 hour. Ethyl iodide (18.40 g, 0.118 mol) was added and stirring was continued for 3 hours. The mixture was poured onto the ice water and the resulting off-white solid was collected by filtration to give 10.0 g (61%) of product m.p. 48-50 C. NMR (DMSO-d6, 300 MHz): delta1.3 (t, J=8.6 Hz, 3H), 4.28 (q, J=8.6 Hz, 2H), 7.25 (m, 2H), 7.60 (m, 2H).
In an ice-bath,To a solution of 2-chloro-1H-benzo[d]imidazole (1.31 mmol) in N,N-dimethylformamide (6 mL) was added NaH (60% dispersion in paraffin, 1.57 mmol). after 20 minutes,Iodoethane (1.57 mmol) was added,The mixture was left at room temperature. 2 hours later,The reaction is quenched with water,Extraction with EtOAc (2x).The resulting organic phase is washed with brine,Dried over Na2SO4 and concentrated to give A2 as a yellow oil.
  • 12
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  • potassium (4-chlorophenyl)trifluoroborate [ No CAS ]
  • [ 1019-85-8 ]
  • 14
  • [ 4857-06-1 ]
  • [ 74-96-4 ]
  • [ 58533-15-6 ]
YieldReaction ConditionsOperation in experiment
92.7% To a solution of 2-chloro-1H- benzo[d]imidazole (1 g, 6.553 mmol) in DMF (50 mL) was added NaH (340.8 mg, 8.519 mmol) at 0 oC. After 15 minutes, bromoethane (1.33 g, 8.519 mmol) was added to the reaction mixture at 0 oC. The reaction mixture was stirred at r.t. for 2 hours. TLC (Petroleum ether/EtOAc = 5/1; silica gel plate) showed complete consumption of the starting material after this time. The mixture was quenched by water at 0 oC. The reaction mixture was extracted with EtOAc (50 mL x 2), washed with brine and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified via column chromatography (Petroleum ether/EtOAc) to give the title compound (1.1 g, 92.7% yield) as a white solid. LC- MS: Calculated exact mass = 180.1; Found [M+H]+ = 181.1.
73% General procedure: 2-Chloro-1H-benzoimidazole (3.04 g, 20 mmol) was dissolved in dry DMF (15 mL) at 0 C, to the solution was added NaH (0.91 g, 22.7 mmol), and the mixture was stirred for 1 h at 0 C, then halide (21.6 mmol) was added. The mixture was stirred overnight at room temperature and was poured into water (50 mL) and stirred for 1 h, filtrated, washed with water and dried to afford 4a-d.
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  • [ 68-12-2 ]
  • [ 2851-13-0 ]
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  • [ 4857-06-1 ]
  • [ 60-34-4 ]
  • [ 2851-13-0 ]
  • 19
  • [ 4857-06-1 ]
  • [ 7191-70-0 ]
  • [ 84946-20-3 ]
  • 20
  • [ 4857-06-1 ]
  • [ 192702-01-5 ]
  • 2-chloro-1-(3-chloro-4-fluorobenzyl)-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
120 mg With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; Step C: The crude 2-chlorobenzimidazole (100 mg, 0.575 mmol, 1 eq) was dissolved in DMF (5 mL) in a reaction vial. Potassium carbonate (95 mg, 0.69 mmol, 1.2 eq) was added to the reaction, followed by <strong>[192702-01-5]4-fluoro-3-chlorobenzylbromide</strong> (0.093 mL, 0.69 mmol, 1.3 eq). The reaction was stirred at room temperature and monitored by LCMS. Upon conversion of the starting material, the reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with water (2*) and a brine solution, dried over magnesium sulfate, and concentrated to afford a crude solid. The crude solid was purified by column chromatography to afford the 2-chloro-1-(3-chloro-4-fluorobenzyl)-1H-benzo[d]imidazole as a white solid (120 mg, 71%).
 

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