2-(3-bromophenyl)acetyl chloride

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (0.295 g, 1.93 mmol) in anhydrous DCM (5 mL) was added dropwise to a stirred suspension of aluminum trichloride (0.714 g, 5.35 mmol) in anhydrous DCM (10 mL) at 0° C., under nitrogen. The resulting suspension was stirred at 0° C. for 10 minutes. A solution of 2-(3-bromophenyl)acetyl chloride (48) (0.500 g, 2.14 mmol) in anhydrous DCM (5 mL) was added dropwise to the stirred suspension at 0° C. The resulting suspension was allowed to warm to room temperature and then stirred at room temperature for a further 18 hours. The reaction mixture was poured onto ice (50 mL) and conc HCl (2 mL). The layers were separated and the aqueous layer extracted with DCM (2×50 mL). The combined organics were washed sequentially with 2M HCl (2×75 mL), water (50 mL), and saturated NaHCO3 (50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product, which was used directly in the next stage; m/z (LC-MS, ESI−), RT=2.46 min (M−H=350.00). to warm to room temperature stirred at room temperature for a further 18 hours The layers were separated the aqueous layer extracted with DCM (2×50 mL) The combined organics were washed sequentially with 2M HCl (2×75 mL), water (50 mL), and saturated NaHCO3 (50 mL) The organic layer was dried over Na2SO4 filtered evaporated to afford crude product, which

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (0.295 g, 1.93 mmol) in anhydrous DCM (5 mL) was added dropwise to a stirred suspension of aluminum trichloride (0.714 g, 5.35 mmol) in anhydrous DCM (10 mL) at 0° C., under nitrogen. The resulting suspension was stirred at 0° C. for 10 minutes. A solution of 2-(3-bromophenyl)acetyl chloride (48) (0.500 g, 2.14 mmol) in anhydrous DCM (5 mL) was added dropwise to the stirred suspension at 0° C. The resulting suspension was allowed to warm to room temperature and then stirred at room temperature for a further 18 hours. The reaction mixture was poured onto ice (50 mL) and conc HCl (2 mL). The layers were separated and the aqueous layer extracted with DCM (2×50 mL). The combined organics were washed sequentially with 2M HCl (2×75 mL), water (50 mL), and saturated NaHCO3 (50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product, which was used directly in the next stage; m/z (LC-MS, ESI−), RT=2.46 min (M−H=350.00). to warm to room temperature stirred at room temperature for a further 18 hours The layers were separated the aqueous layer extracted with DCM (2×50 mL) The combined organics were washed sequentially with 2M HCl (2×75 mL), water (50 mL), and saturated NaHCO3 (50 mL) The organic layer was dried over Na2SO4 filtered evaporated to afford crude product, which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Thionyl chloride (2.035 mL, 27.90 mmol) was added to 2-(3-bromophenyl)acetic acid (1.500 g, 6.98 mmol) in DCM (30 mL). The resulting solution was stirred at room temperature for 18 hours. The resulting mixture was evaporated to dryness and the residue was azeotroped with toluene to afford crude product (1.570 g, 96% yield), which was used without further purification. The resulting mixture was evaporated to dryness the residue was azeotroped with toluene

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The raw material meta-bromophenylacetic acid (100 g, 0.47 mol, 1.0 eq) was dissolved in dichloromethane (500 ml), then was cooled to 0° C. in ice-salt bath. Oxalyl chloride (120 g, 0.95 mol, 2.0 eq) was added dropwise to the reaction mixture with temperature maintaining 0° C. After the dropping was finished, the reaction temperature was changed to room temperature and reacted for two hours. The reaction mixture was concentrated under reduced pressure to obtain meta-bromophenylacetyl chloride (110 g, 0.47 mol) after the reaction completed. The obtained meta-bromophenylacetyl chloride was dissolved in dichloromethane (200 ml) for further use. was changed to room temperature reacted for two hours The reaction mixture was concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 2-amino-4-chloro-5-nitrobenzoic acid methyl ester (Example 9, 780 mg in 10 mL dichloroethane) was added a solution of (3-bromophenyl)acetyl chloride (prepared essentially as described in Example 9, 866 mg in 5 mL dichloroethane) and the mixture heated to reflux on an oil bath. After 18 hours, the reaction mixture was concentrated in vacuo and the title compound obtained by crystallization from methanol (1.18 g). prepared essentially heated to reflux on an oil bath the reaction mixture was concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared in an analogous manner as described for intermediate B3A from (3-bromo-phenyl)-acetyl chloride (intermediate B2B) (12.1 g, ca. 50 mmol). The compound was obtained after silica gel column chromatography with n-heptane/ethyl acetate as a light yellow liquid (7.934 g, 62%). MS (ISP): m/z=272.1 [(M+NH4)+] and 274.1 [(M+2+NH4)+]

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (0.295 g, 1.93 mmol) in anhydrous DCM (5 mL) was added dropwise to a stirred suspension of aluminum trichloride (0.714 g, 5.35 mmol) in anhydrous DCM (10 mL) at 0° C., under nitrogen. The resulting suspension was stirred at 0° C. for 10 minutes. A solution of 2-(3-bromophenyl)acetyl chloride (48) (0.500 g, 2.14 mmol) in anhydrous DCM (5 mL) was added dropwise to the stirred suspension at 0° C. The resulting suspension was allowed to warm to room temperature and then stirred at room temperature for a further 18 hours. The reaction mixture was poured onto ice (50 mL) and conc HCl (2 mL). The layers were separated and the aqueous layer extracted with DCM (2×50 mL). The combined organics were washed sequentially with 2M HCl (2×75 mL), water (50 mL), and saturated NaHCO3 (50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product, which was used directly in the next stage; m/z (LC-MS, ESI−), RT=2.46 min (M−H=350.00). to warm to room temperature stirred at room temperature for a further 18 hours The layers were separated the aqueous layer extracted with DCM (2×50 mL) The combined organics were washed sequentially with 2M HCl (2×75 mL), water (50 mL), and saturated NaHCO3 (50 mL) The organic layer was dried over Na2SO4 filtered evaporated to afford crude product, which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Thionyl chloride (2.035 mL, 27.90 mmol) was added to 2-(3-bromophenyl)acetic acid (1.500 g, 6.98 mmol) in DCM (30 mL). The resulting solution was stirred at room temperature for 18 hours. The resulting mixture was evaporated to dryness and the residue was azeotroped with toluene to afford crude product (1.570 g, 96% yield), which was used without further purification. The resulting mixture was evaporated to dryness the residue was azeotroped with toluene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine 3-propoxy-benzylamine in 50 mL of dichloromethane and add dropwise to a mixture of 3-bromophenylacetyl chloride (4.90 gm; 21.0 mmol) and triethylamine (3.60 gm; 35.9 mmol) in 250 mL of dichloromethane at 0° C. Allow the reaction to warm to room temperature and stir for 18 h. Pour the reaction into 100 mL of saturated brine, separate the layers and extract the aqueous layer with 100 ml of dichloromethane. Combine organic layers, wash with brine, dry (MgSO4), and concentrate. Purification by chromatography on silica gel with 40% EtOAc in hexanes gives the title compound. the reaction Pour separate the layers extract the aqueous layer with 100 ml of dichloromethane Combine organic layers, wash with brine dry (MgSO4) concentrate Purification by chromatography on silica gel with 40% EtOAc in hexanes