1-(2,4-difluorophenyl)propan-2-one

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

Procedure: 5 mmol of sodium 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanolate and 10 mmol of (2,4-difluorophenyl)propanone are treated as described in Example 61 (method A).

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

Procedure: (S)-ethyl 2-tert-butoxy-2-(5,7-difluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate was prepared in a similar was as (S)-ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate in Example 20, except using 1-(2,4-difluorophenyl)propan-2-one instead of 1-(3-bromophenyl)propan-2-one. 1H-NMR: 400 MHz, (CDCl3) δ: 7.82 (s, 1H), 7.39 (d, J=5.47 Hz, 1H), 6.99 (m, 1H), 5.63 (s, 1H), 4.18 (m, 2H), 2.49 (s, 3H), 1.11 (s+t, 12H). 19F-NMR: 377 MHz, (CDCl3) δ: −73.27 (s, 3F), −109.1 (m, 1F), −117.5 (m, 1F).

Conditions: temp:32.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 140.2 g (0.80 mol) of 1-(2,4-difluoro-phenyl)-propane-2-one in 550 g of methylcyclohexane is warmed up to 30-35° C. Over a period of 2 hours 96.6 g (0.80 mol) of isoamyl nitrite is added while a slow stream of dry hydrogen chloride is fed subsurface into the reactor. Following the end of the addition the batch is stirred for 15 minutes at 30-35° C. before the suspension is cooled to 0° C. The product is isolated by filtration and the filter cake is washed with 150 g of methylcyclohexane at 0° C.: 146.9 g of (E)-1-(2,4-difluoro-phenyl)-propane-1,2-dione 1-oxime (mp. 133-135° C.) are obtained in 89.5% yield. the end of the addition the batch is cooled to 0° C The product is isolated by filtration the filter cake is washed with 150 g of methylcyclohexane at 0° C.

Conditions: temp:32.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 140.2 g (0.80 mol) of 1-(2,4-difluoro-phenyl)-propane-2-one in 550 g of methylcyclohexane is warmed up to 30-35° C. Over a period of 2 hours 96.6 g (0.80 mol) of isoamyl nitrite is added while a slow stream of dry hydrogen chloride is fed subsurface into the reactor. Following the end of the addition the batch is stirred for 15 minutes at 30-35° C. before the suspension is cooled to 0° C. The product is isolated by filtration and the filter cake is washed with 150 g of methylcyclohexane at 0° C.: 146.9 g of (E)-1-(2,4-difluoro-phenyl)-propane-1,2-dione 1-oxime (mp. 133-135° C.) are obtained in 89.5% yield. the end of the addition the batch is cooled to 0° C The product is isolated by filtration the filter cake is washed with 150 g of methylcyclohexane at 0° C.

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

Procedure: 5 mmol of sodium 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanolate and 10 mmol of (2,4-difluorophenyl)propanone are treated as described in Example 61 (method A).

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

Procedure: (S)-ethyl 2-tert-butoxy-2-(5,7-difluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate was prepared in a similar was as (S)-ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate in Example 20, except using 1-(2,4-difluorophenyl)propan-2-one instead of 1-(3-bromophenyl)propan-2-one. 1H-NMR: 400 MHz, (CDCl3) δ: 7.82 (s, 1H), 7.39 (d, J=5.47 Hz, 1H), 6.99 (m, 1H), 5.63 (s, 1H), 4.18 (m, 2H), 2.49 (s, 3H), 1.11 (s+t, 12H). 19F-NMR: 377 MHz, (CDCl3) δ: −73.27 (s, 3F), −109.1 (m, 1F), −117.5 (m, 1F).

Conditions: temp:32.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 140.2 g (0.80 mol) of 1-(2,4-difluoro-phenyl)-propane-2-one in 550 g of methylcyclohexane is warmed up to 30-35° C. Over a period of 2 hours 96.6 g (0.80 mol) of isoamyl nitrite is added while a slow stream of dry hydrogen chloride is fed subsurface into the reactor. Following the end of the addition the batch is stirred for 15 minutes at 30-35° C. before the suspension is cooled to 0° C. The product is isolated by filtration and the filter cake is washed with 150 g of methylcyclohexane at 0° C.: 146.9 g of (E)-1-(2,4-difluoro-phenyl)-propane-1,2-dione 1-oxime (mp. 133-135° C.) are obtained in 89.5% yield. the end of the addition the batch is cooled to 0° C The product is isolated by filtration the filter cake is washed with 150 g of methylcyclohexane at 0° C.