Benzene,1,3-dibroMo-5-ethyl-

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1,3-dibromo-5-ethylbenzene (2.7 g, 10.2 mmol), copper cyanide (0.916 g, 10.2 mmol), pyridine (1.65 mL, 20.5 mmol) in DMF (15 mL) was heated at 150° C. for 3 h. After cooling to r.t., the mixture was poured into a solution of H2O (30 mL) and ammonia (25% aq. Solution, 20 mL) and extracted with EtOAc. The combined organic layer was dried (MgSO4), filtered and concentrated in vacuo. The product was purified using flash chromatography on silica gel, gradient elution of 0-60% EtOAc in n-heptane. GCMS (CI) m/z 210 [M+1]+. After cooling to r.t. extracted with EtOAc The combined organic layer was dried (MgSO4) filtered concentrated in vacuo The product was purified on silica gel, gradient elution of 0-60% EtOAc in n-heptane

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1,3-dibromo-5-ethylbenzene (2.7 g, 10.2 mmol), copper cyanide (0.916 g, 10.2 mmol), pyridine (1.65 mL, 20.5 mmol) in DMF (15 mL) was heated at 150° C. for 3 h. After cooling to r.t., the mixture was poured into a solution of H2O (30 mL) and ammonia (25% aq. Solution, 20 mL) and extracted with EtOAc. The combined organic layer was dried (MgSO4), filtered and concentrated in vacuo. The product was purified using flash chromatography on silica gel, gradient elution of 0-60% EtOAc in n-heptane. GCMS (CI) m/z 210 [M+1]+. After cooling to r.t. extracted with EtOAc The combined organic layer was dried (MgSO4) filtered concentrated in vacuo The product was purified on silica gel, gradient elution of 0-60% EtOAc in n-heptane

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1,3-dibromo-5-ethylbenzene (2.7 g, 10.2 mmol), copper cyanide (0.916 g, 10.2 mmol), pyridine (1.65 mL, 20.5 mmol) in DMF (15 mL) was heated at 150° C. for 3 h. After cooling to r.t., the mixture was poured into a solution of H2O (30 mL) and ammonia (25% aq. Solution, 20 mL) and extracted with EtOAc. The combined organic layer was dried (MgSO4), filtered and concentrated in vacuo. The product was purified using flash chromatography on silica gel, gradient elution of 0-60% EtOAc in n-heptane. GCMS (CI) m/z 210 [M+1]+. After cooling to r.t. extracted with EtOAc The combined organic layer was dried (MgSO4) filtered concentrated in vacuo The product was purified on silica gel, gradient elution of 0-60% EtOAc in n-heptane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Compound of 1,3-dibromo-5-ethyl-benzene is reacted with 3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester as in Example 18 to afford 0.898 g (56%) of the title compound. Rf=0.32 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C19H21O3Br 376, found 377 and 379 (M+1 and M+3, 100%).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1,3-dibromo-5-vinyl-benzene (4.55 g, 17.4 mmol) and 20% Pd(OH)2/C (2.0 g) in THF (60 mL) is purged with N2 and then H2, and the mixture is stirred under a H2 balloon at rt for 5 hours. The mixture is filtered through hyflo, and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 15/1 hexanes/ethyl acetate to afford 3.38 g (74%) of the title compound. Rf=0.63 (9/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3). is purged with N2 The mixture is filtered through hyflo the solvent is removed in vacuo to afford crude product that is absorbed on silica gel purified by flash chromatography

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1,3-dibromo-5-ethylbenzene (2.7 g, 10.2 mmol), copper cyanide (0.916 g, 10.2 mmol), pyridine (1.65 mL, 20.5 mmol) in DMF (15 mL) was heated at 150° C. for 3 h. After cooling to r.t., the mixture was poured into a solution of H2O (30 mL) and ammonia (25% aq. Solution, 20 mL) and extracted with EtOAc. The combined organic layer was dried (MgSO4), filtered and concentrated in vacuo. The product was purified using flash chromatography on silica gel, gradient elution of 0-60% EtOAc in n-heptane. GCMS (CI) m/z 210 [M+1] After cooling to r.t. extracted with EtOAc The combined organic layer was dried (MgSO4) filtered concentrated in vacuo The product was purified on silica gel, gradient elution of 0-60% EtOAc in n-heptane

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1,3-dibromo-5-ethylbenzene (2.7 g, 10.2 mmol), copper cyanide (0.916 g, 10.2 mmol), pyridine (1.65 mL, 20.5 mmol) in DMF (15 mL) was heated at 150° C. for 3 h. After cooling to r.t., the mixture was poured into a solution of H2O (30 mL) and ammonia (25% aq. Solution, 20 mL) and extracted with EtOAc. The combined organic layer was dried (MgSO4), filtered and concentrated in vacuo. The product was purified using flash chromatography on silica gel, gradient elution of 0-60% EtOAc in n-heptane. GCMS (CI) m/z 210 [M+1]+. After cooling to r.t. extracted with EtOAc The combined organic layer was dried (MgSO4) filtered concentrated in vacuo The product was purified on silica gel, gradient elution of 0-60% EtOAc in n-heptane