4-(bromomethyl)benzoyl chloride

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

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

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

Procedure: p-Bromomethyl benzoic acid (10.5 g., 0.05 moles) is charged to a round-bottom flask equipped with a magnetic stirrer. Thionyl chloride (50 ml.) is added thereto and the mixture heated under reflux with stirring. After approximately 10 minutes the solid material is dissolved. The heating under reflux is continued for an additional 30 minutes, the clear solution stoppered and cooled in a dry atmosphere. The excess thionyl chloride is removed using a rotary evaporator to yield p-bromomethyl benzoyl chloride (m.p. 56°-58°). This product is not further purified but utilized in the next stage of the reaction. equipped with a magnetic stirrer the mixture heated under reflux After approximately 10 minutes the solid material is dissolved The heating under reflux cooled in a dry atmosphere The excess thionyl chloride is removed a rotary evaporator

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

Procedure: A solution of 19.5 grams of alpha-bromo-p-toluoyl chloride in 100 ml of methylene chloride is added to a solution of 15.7 ml of triethylamine in 100 ml of methanol. The reaction mixture is stirred overnight at room temperature and then concentrated. The residue is dissolved in ether, washed with water and the ether evaporated to give the intermediate p-methoxycarbonylbenzyl bromide. concentrated The residue is dissolved in ether washed with water the ether evaporated

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

Procedure: In 30 ml of benzene was dissolved 2.3 g of 4-bromomethylbenzoic acid chloride, 1.37 g of n-octyl alcohol and 5 ml of triethylamine were added to the solution, and a reaction was carried out at room temperature with stirring overnight. Then, 30 ml of ethyl acetate and 10 ml of 2N HCl were added to the reaction mixture, and the organic layer was separated, washed with water and dried on magnesium sulfate. The solvent was removed by distillation, and the residue was separated and purified by the silica gel column chromatography to obtain 3.0 g of octyl 4-bromomethylbenzoate. were added to the solution was carried out at room temperature the organic layer was separated washed with water dried on magnesium sulfate The solvent was removed by distillation the residue was separated purified by the silica gel column chromatography

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 4-(bromomethyl)benzoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2-[4-(bromomethyl)phenyl]ethanoyl isothiocyanate was prepared using the resultant 4-(bromomethyl)-1-benzenecarbonyl chloride as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 2-[4-(bromomethyl)phenyl]ethanoyl isothiocyanate in ethanol (1 ml) was then added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (50 mg, yield 52%). The solvent was removed by distillation, and 2-[4-(bromomethyl)phenyl]ethanoyl isothiocyanate was prepared The reaction solution was concentrated the residue was purified by chromatography on silica gel

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 4-(bromomethyl)benzoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2-[4-(bromomethyl)phenyl]ethanoyl isothiocyanate was prepared using the resultant 4-(bromomethyl)-1-benzenecarbonyl chloride as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 2-[4-(bromomethyl)phenyl]ethanoyl isothiocyanate in ethanol (1 ml) was then added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (50 mg, yield 52%). The solvent was removed by distillation, and 2-[4-(bromomethyl)phenyl]ethanoyl isothiocyanate was prepared The reaction solution was concentrated the residue was purified by chromatography on silica gel

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

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

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-bromomethyl-benzoyl chloride (7.0 g, 30.24 mmol), polyvinyl pyridine (9.6 g, 90.7 mmol) and dimethyl amine (15.9 ml, 31.8 mmol, 2.0 M in THF) was stirred at 23° C. for 15 h. The solution was filtered and the solvent removed to give 7.3 g (99% yield) of 4-bromomethyl-N,N-dimethyl-benzamide as a yellow solid. The solution was filtered the solvent removed

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

Procedure: 4-bromomethylbenzoic acid (25 g, 116.25 mmol) was dissolved in CH2Cl2 (200 ml) and treated with oxalyl chloride (12.2 ml, 139.5 mmol). DMF (0.45 ml) was added slowly then stirred for 1 h. The solvent was removed to give the 4-bromomethylbenzoyl chloride as a white solid. The solvent was removed

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

Procedure: A solution of the title A compound, 4-bromomethyl-benzoyl chloride (466 mg, 2 mmol) in 3 mL of CH2Cl2 is added dropwise to a solution of 2-ethyl-1-butanol (204 mg, 2 mmol) and TEA (202 mg, 2 mmol) in 10 mL of CH2Cl2 at 0˜5° C. over 30 min. The reaction is allowed to warm to RT and stirred overnight. The solvent is evaporated and the residue is partitioned between hexane and water. The organic phase is dried over anhydrous MgSO4 and concentrated. The residue is chromatographic on silica gel using EtOAc/hexane (gradient 90-70) to give 4-bromomethyl-benzoic acid 2-ethyl-butyl ester as a colorless oil. The solvent is evaporated the residue is partitioned between hexane and water The organic phase is dried over anhydrous MgSO4 concentrated