1-fluoro-4-methoxybenzene

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:

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: 4-Fluoroanisole (20 g) and ethyl succinyl chloride (28 g) were dissolved in nitromethane (70 ml). The solution was cooled in an ice +water bath and stirred under nitrogen. Aluminium chloride was added (30 g in 3×10 g portions) over 30 minutes. The cooling bath was removed and the reaction mixture was stirred under nitrogen for 5 hours. The reaction mixture was poured onto ice and extracted into ethyl acetate. The organic phase was collected and concentrated under reduced pressure. The crude product was taken up in ethyl acetate (150 ml) and washed with 2N sodium hydroxide solution (2×100 ml). The organic phase was dried over magnesium sulphate, filtered and the solvent removed under reduced pressure. The product was dissolved in acetic acid (200 ml) containing 47% perchloric acid (10 ml) and hydrogenated over 10% palladium on charcoal until two equivalents of hydrogen were taken up. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was taken up in ethyl acetate and water. Sodium hydrogen carbonate was added until no reaction occurred then the organic phase was collected, dried and filtered. The solvent was removed at reduced pressure and the resulting dark oil was dissolved in methanol (120 ml). Sodium hydroxide (8 g) was added and the mixture was heated under reflux for 3 hours. Water (50 ml) was added and the mixture was washed with 1:1 ether/hexane (150 ml). The aqueous phase was acidified and the product was extracted into ethyl acetate. The organic phase was dried, filtered and evaporated under reduced pressure to give the product (19.5 g), as a dark oil that solidified on standing. The solution was cooled in an ice +water bath The cooling bath was removed the reaction mixture was stirred under nitrogen for 5 hours The reaction mixture was poured onto ice extracted into ethyl acetate The organic phase was collected concentrated under reduced pressure washed with 2N sodium hydroxide solution (2×100 ml) The organic phase was dried over magnesium sulphate filtered the solvent removed under reduced pressure The product was dissolved in acetic acid (200 ml) containing 47% perchloric acid (10 ml) The reaction mixture was filtered concentrated under reduced pressure Sodium hydrogen carbonate was added until no reaction the organic phase was collected dried filtered The solvent was removed at reduced pressure the resulting dark oil was dissolved in methanol (120 ml) Sodium hydroxide (8 g) was added the mixture was heated under reflux for 3 hours Water (50 ml) was added the mixture was washed with 1:1 ether/hexane (150 ml) the product was extracted into ethyl acetate The organic phase was dried filtered evaporated under reduced pressure

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 100 ml of 1,2-dichloroethane, maleic anhydride (11.3 g, 114 mmol) and anhydrous aluminum chloride (31.0 g, 228 mmol) were dissolved by heating at 50° C. for 15 minutes, and then p-fluoroanisole (12.6 g, 100 mmol) was added dropwise. The mixture was refluxed for an hour and then poured into 60 ml of concentrated hydrochloric acid with 400 g of cracked ice. Resulting crystals deposited out therein were obtained through a filtration, washed with water and dried in vacuo to give 16.0 g (80.0%) of the subject desired compound as yellow crystals. The mixture was refluxed for an hour Resulting crystals out therein were obtained through a filtration washed with water dried in vacuo to give 16.0 g (80.0%) of the

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

Procedure: A reaction of 4-t-butylcyclohexanone (2 mmol) with diethylaminosulfur trifluoride (3.0 mmol) in CH2Cl2 (10 mL) containing TiCl4 (0.3 mmol) at room temperature gave a 99% conversion of starting material to products and a 67% yield of 1,1-difluoro-4-t-butylcyclohexane after 6 h. as determined by NMR (4-fluoroanisole as internal standard). gave a 99% conversion of starting material to products

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

Procedure: A reaction of 4-t-butylcyclohexanone (2 mmol) with diethylaminosulfur trifluoride (3.0 mmol) in CH2Cl2 (10 mL) containing Znl2 (0.3 mmol) at room temperature gave a 99% conversion of starting material to products and a 67% yield of 1,1-difluoro-4-t-butylcyclohexane after 6 h. as determined by NMR (4-fluoroanisole as internal standard). containing Znl2 (0.3 mmol) at room temperature gave a 99% conversion of starting material to products

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

Procedure: A reaction of 4-t-butylcyclohexanone (2 mmol) with diethylaminosulfur trifluoride (3.0 mmol) in CH2Cl2 (10 mL) containing BF3.OEt2 (0.3 mmol) at room temperature gave a 99% conversion of starting material to products and a 67% yield of 1,1-difluoro-4-t-butylcyclohexane after 6 h. as determined by NMR (4-fluoroanisole as internal standard). gave a 99% conversion of starting material to products