2-溴-6-氟甲苯衍生物的合成

Synthesis of 2-Bromo-6-fluorotoluene Derivates

以2-溴-6-氟甲苯为原料,经溴化反应和氧化反应分别合成了2-溴-6-氟溴苄和2-溴-6-氟苯甲酸。再以2-溴-6-氟溴苄为原料,经水解和Sommlet反应分别合成了2-溴-6-氟苯甲醇和2-溴-6-氟苯甲醛,并对各工艺条件进行了优化。结果表明,以HBr/H2O2为溴化试剂,2-溴-6-氟溴苄收率为90.3%;以乙醇为溶剂,2-溴-6-氟苯甲醇收率为92.8%;以KMnO4作为氧化剂,2-溴-6-氟苯甲酸收率为58.2%;当n(2-溴-6-氟溴苄)∶n(六亚甲基四胺)=1∶1.3时,2-溴-6-氟苯甲醛收率为79.0%。各产物结构经红外、核磁共振等技术得到了确证。

2-Bromo-6-fluorobenzyl bromide and 2-bromo-6-fluorobenzoic acid were prepared from 2- bromo-6-fluorotoluene by bromination and oxidation reactions. And then 2-bromo-6-fluorophenyl methanol and 2-bromo-6-fluorobenzaldehyde were prepared from 2-bromo-6-fluorobenzyl bromide by hydrolysis and Sommlet reactions. The synthesis process was studied in this paper. The results show that, when HBr/H202 was used as brominate agent, the yield of 2-bromo-6-fluorobenzyl bromide was 90.3% ;when ethanol was used as solvent,the yield of 2-bromo-6-fluorophenyl methanol was 92.8%. In the oxidation reaction, the yield of 2-bromo-6-fluorobenzoic acid was 58. 2% with KMnO4 as oxidant. Under the condition of n （ 2-bromo-6-fluoro benzyl bromide ） ： n （ methenamine ） = 1 ： 1.3, the yield of 2-bromo-6-fluorobenzaldehyde was 79.0%. The structures of all products were characterized by means of nuclear magnetic resonance and infrared.