231297-62-4

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: The title compound was prepared from 4-acetyl-1-chloro-2-fluorobenzene according to the procedure for preparing 4-(trifluoromethoxy)phenacyl bromide described in Example 189.

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

Procedure: The title compound was prepared according to the procedure described in Example 57 from methyl trans-4-chloro-2-(phenylsulfonylamino)cinnamate (step 1 of Example 8, Method A) and 4-chloro-3-fluorophenacyl bromide* .

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

Procedure: The title compound was prepared from 4-acetyl-1-chloro-2-fluorobenzene according to the procedure for preparing 4-(trifluoromethoxy)phenacyl bromide described in Example 189.

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

Procedure: The title compound was prepared according to the procedure described in Example 57 from methyl trans-4-chloro-2-(phenylsulfonylamino)cinnamate (step 1 of Example 8, Method A) and 4-chloro-3-fluorophenacyl bromide* .

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

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

Procedure: The title compound was prepared according to the procedure described in Example 57 from methyl trans-4-chloro-2-(phenylsulfonylamino)cinnamate (step 1 of Example 8, Method A) and 4-chloro-3-fluorophenacyl bromide* .

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

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

Procedure: In the same manner as described in step 4 of Example 78, using 2-bromo-1-(4-chloro-3-fluoro-phenyl)-ethanone (2.7 g, 10.7 mmol), prepared in the previous step, and potassium isothiocyanate (1.25 g, 12.8 mmol) in ethanol (150 mL) the crude product was collected by suction filtration to give 1-(4-chloro-3-fluoro-phenyl)-2-thiocyanato-ethanone (2.47 g, 100%), which was used in the next step without further purification. MS (ES) m/z 230[M+H+]. was collected by suction filtration

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

Procedure: To a solution of 1-(4-chloro-3-fluorophenyl)ethanone (3.4 g, 19.7 mmol), prepared in the previous step, in methylene chloride:methanol (1:3) was added tetrabutylammonium tribromide (9.5 g, 19.7 mmol) in portions. The reaction was monitored by TLC (3:1 hexane:ethyl acetate) until the starting material was consumed. The reaction solution was concentrated in vacuo and the residue was partitioned between diethyl ether and water. The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 4.2 g of crude product. The crude product was purified on silica gel using 5% ethyl acetate:hexane to give 2-bromo-1-(4-chloro-3-fluoro-phenyl)-ethanone (3.4 g, 69%) as desired product, MS (ES) m/z 252 [M+H+]. was consumed The reaction solution was concentrated in vacuo the residue was partitioned between diethyl ether and water The layers were separated the organic layer was dried over anhydrous sodium sulfate filtered concentrated in vacuo to give 4.2 g of crude product The crude product was purified on silica gel using 5% ethyl acetate

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

Procedure: The title compound was prepared from 4-acetyl-1-chloro-2-fluorobenzene according to the procedure for preparing 4-(trifluoromethoxy)phenacyl bromide described in Example 189.