2-bromo-4-fluoro-1-methylbenzene

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

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

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: A mixture of 18.9 g (100 mmol) of 2-bromo-4-fluorotoluene, 17.8 g (100 mmol) of N-bromosuccinimide, 400 mg of benzoyl peroxide, and 200 ml of CCl4 were refluxed for 2 h. The reaction mixture was filtered through a glass frit (G2), and the precipitate was additionally washed with 3×50 ml of CCl4. The combined filtrate was evaporated to dryness. Fractional distillation of the residue (bp 92-96° C./4 mm Hg) gave the title product as colorless oil. Yield 20.4 g (76%). were refluxed for 2 h The reaction mixture was filtered through a glass frit (G2) the precipitate was additionally washed with 3×50 ml of CCl4 The combined filtrate was evaporated to dryness Fractional distillation of the residue (bp 92-96° C./4 mm Hg)

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

Procedure: A mixture of 18.9 g (100 mmol) of 2-bromo-4-fluorotoluene, 17.8 g (100 mmol) of N-bromosuccinimide, 400 mg of benzoyl peroxide, and 200 ml of CCl4 were refluxed for 2 h. The reaction mixture was filtered through a glass frit (G2), and the precipitate was additionally washed with 3×50 ml of CCl4. The combined filtrate was evaporated to dryness. Fractional distillation of the residue (bp 92-96° C./4 mm Hg) gave the title product as colorless oil. Yield 20.4 g (76%). were refluxed for 2 h The reaction mixture was filtered through a glass frit (G2) the precipitate was additionally washed with 3×50 ml of CCl4 The combined filtrate was evaporated to dryness Fractional distillation of the residue (bp 92-96° C./4 mm Hg)

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

Procedure: By the method of Example 7, Step C, 75 g (0.40 mole) of 2-bromo-4-fluorotoluene, 70.6 g (0.40 mole) of N-bromosuccinimide, and 2.5 g (0.03 mole) of benzoyl peroxide were reacted in 450 ml of carbon tetrachloride, yielding 107.8 g of impure 2-bromo-4-fluorobenzyl bromide (68% assay).

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Bromo-4-fluorotoluene (10.215 g) was dissolved in ethyl acetate (100 ml), N-bromosuccinimide (11.3 g) and 70% benzoyl peroxide (200 mg) were added thereto, and the resulting mixture was stirred under heating at 80° C. for 1 hr. After the reaction solution was cooled, the resulting insoluble matters were filtered off. The resulting filtrate was washed with an aqueous solution of saturated sodium bicarbonate, dried (over MgSO4) and evaporated. The resulting residue was dissolved in acetic acid (30 ml), water (30 ml) and hexamethylene tetramine (15.141 g) were added thereto, and the resulting mixture was heated under stirring at 100° C. for 1 hr. To the mixture was added 38% hydrochloric acid (20 ml), which was then stirred for 1 hr, and then it was cooled as it was, and extracted with ethyl acetate. The resulting organic phase was washed with an aqueous solution of saturated sodium bicarbonate, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a colorless solid (4.376 g, yield; 41%). After the reaction solution was cooled the resulting insoluble matters were filtered off The resulting filtrate was washed with an aqueous solution of saturated sodium bicarbonate dried (over MgSO4) evaporated The resulting residue was dissolved in acetic acid (30 ml) water (30 ml) and hexamethylene tetramine (15.141 g) were added the resulting mixture was heated under stirring at 100° C. for 1 hr To the mixture was added 38% hydrochloric acid (20 ml), which was then stirred for 1 hr it was cooled as it extracted with ethyl acetate The resulting organic phase was washed with an aqueous solution of saturated sodium bicarbonate dried (over MgSO4) evaporated The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Bromo-4-fluorotoluene (10.215 g) was dissolved in ethyl acetate (100 ml), N-bromosuccinimide (11.3 g) and 70% benzoyl peroxide (200 mg) were added thereto, and the resulting mixture was stirred under heating at 80° C. for 1 hr. After the reaction solution was cooled, the resulting insoluble matters were filtered off. The resulting filtrate was washed with an aqueous solution of saturated sodium bicarbonate, dried (over MgSO4) and evaporated. The resulting residue was dissolved in acetic acid (30 ml), water (30 ml) and hexamethylene tetramine (15.141 g) were added thereto, and the resulting mixture was heated under stirring at 100° C. for 1 hr. To the mixture was added 38% hydrochloric acid (20 ml), which was then stirred for 1 hr, and then it was cooled as it was, and extracted with ethyl acetate. The resulting organic phase was washed with an aqueous solution of saturated sodium bicarbonate, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a colorless solid (4.376 g, yield; 41%). After the reaction solution was cooled the resulting insoluble matters were filtered off The resulting filtrate was washed with an aqueous solution of saturated sodium bicarbonate dried (over MgSO4) evaporated The resulting residue was dissolved in acetic acid (30 ml) water (30 ml) and hexamethylene tetramine (15.141 g) were added the resulting mixture was heated under stirring at 100° C. for 1 hr To the mixture was added 38% hydrochloric acid (20 ml), which was then stirred for 1 hr it was cooled as it extracted with ethyl acetate The resulting organic phase was washed with an aqueous solution of saturated sodium bicarbonate dried (over MgSO4) evaporated The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

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

Procedure: To a solution of 2-bromo-4-fluorotoluene (50 g, 265 mmol) in CCl4 (1 L) was added NBS (52 g, 291 mmol) and 300 mg of benzoyl peroxide. The mixture was heated to reflux and stirred for 30 minutes under a sun lamp. The reaction mixture was cooled and filtered on a SiO2 pad eluted with hexanes. The filtrate was concentrated to give 70 g of the title compound as a colorless oil and used as such. The mixture was heated to reflux The reaction mixture was cooled filtered on a SiO2 pad eluted with hexanes The filtrate was concentrated

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

Procedure: A mixture of 2-Bromo-4-Fluorotoluene (46.6 g, 0.25 mol, Aldrich), N-bromosuccinimide (46.3 g, 0.26 mol, Aldrich) and benzoyl peroxide (0.5 g, 0.002 mol, Aldrich) in carbon tetrachloride (500 ml) was refluxed and illuminated (250 watt, infrared lamp) for 18 h. After cooling to room temperature, the succinimide was filtered and the filtrate was concentrated in vacuo. Chromatography on silica gel with hexanes as eluent gave 41.8 g (62%) of 2-bromo-1-(bromomethyl)-4-fluorobenzene as a white solid: mp 47°-49° C. was refluxed illuminated (250 watt, infrared lamp) for 18 h the succinimide was filtered the filtrate was concentrated in vacuo

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

Procedure: A mixture of 2-Bromo-4-Fluorotoluene (46.6 g, 0.25 mol, Aldrich), N-bromosuccinimide (46.3 g, 0.26 mol, Aldrich) and benzoyl peroxide (0.5 g, 0.002 mol, Aldrich) in carbon tetrachloride (500 ml) was refluxed and illuminated (250 watt, infrared lamp) for 18 h. After cooling to room temperature, the succinimide was filtered and the filtrate was concentrated in vacuo. Chromatography on silica gel with hexanes as eluent gave 41.8 g (62%) of 2-bromo-1-(bromomethyl)-4-fluorobenzene as a white solid: mp 47°-49° C. was refluxed illuminated (250 watt, infrared lamp) for 18 h the succinimide was filtered the filtrate was concentrated in vacuo