反应 #2439925

反应方程式

p-fluorphenylboronic acid

3-bromo-5-hydroxymethyl-pyridine

Na2CO3

→

3-(p-fluorophenyl)-5-hydroxymethyl-pyridine

收率 84.4%

溶剂

toluene

反应条件

后处理

1. 1
   其他the biphasic reaction mixture
2. 2
   温度was cooled
3. 3
   其他the organic layer was collected
4. 4
   洗涤washed with saturated NaCl
5. 5
   洗涤The aqueous layer was washed with EtOAc
6. 6
   其他the combined organic layers were dried on Na2SO4
7. 7
   其他The drying agent was removed by filtration
8. 8
   其他the solvent was evaporated in vacuo
9. 9
   其他to give a dark oil which
10. 10
    其他was purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH/NH4OH, 95/4.5/0.5)

实验过程

To a solution of 3-bromo-5-hydroxymethyl-pyridine (3.3 g, 17.5 mmol) in toluene (35 ml) was added Pd(PPh3)4 (0.6 g, 0.52 mmol), an aqueous solution of Na2CO3 (17.5 ml of a 2M solution) and p-fluorphenylboronic acid (2.65 g, 19 mmol, dissolved in 8.5 ml EtOH). The mixture was heated at 80-90° C. for 1 hr and vigorously stirred. After the reaction was completed, the biphasic reaction mixture was cooled, the organic layer was collected and washed with saturated NaCl. The aqueous layer was washed with EtOAc and the combined organic layers were dried on Na2SO4. The drying agent was removed by filtration and the solvent was evaporated in vacuo to give a dark oil which was purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH/NH4OH, 95/4.5/0.5) and yielded 3-(p-fluorophenyl)-5-hydroxymethyl-pyridine (3.0 g, 84%). The product was converted into its monohydrochloride salt; the residue was dissolved in Et2O and treated with 16.5 eq of ethanolic HCl. The product 3-(p-fluorophenyl)-5-hydroxymethyl-pyridinium hydrochloride Q4-OH.HCl precipitated as a white solid which was collected by filtration and subsequent drying.

来源