The invention discloses a preparation method of a 
silodosin key intermediate, and belongs to the technical field of 
medicine synthesis. Carrying out Friedel-Crafts reaction on 
indoline and trichloroacetonitrile to obtain a compound 1; brominating to obtain a compound 2; then carrying out substitution with 2-(3-bromopropoxy) tetrahydro-2H-
pyran to obtain a compound 3; then carrying out 
nucleophilic addition with (S)-epoxypropane or (R)-epoxypropane at an ultralow temperature to obtain a compound 4; then carrying out 
Mitsunobu reaction with 
phthalimide to obtain a compound 5 (configuration inversion) or esterifying with paratoluensulfonyl 
chloride, and reacting with 
potassium phthalimide under the condition of inorganic alkali to obtain the compound 5; reducing through hydrazine 
hydrate to obtain a compound 6; then removing 
tetrahydropyran protection from p-toluenesulfonic acid to obtain a compound 7; performing amino Boc protection under an alkaline condition to obtain a compound 8; esterifying with 
benzoyl chloride to obtain a compound 9; removing Boc protection with 
hydrochloric acid to obtain a compound 10; and salifying with L-
tartaric acid to obtain a compound 11. Compared with the prior art, the preparation method has the advantages that cyano groups synthesized by Vilsmeier reaction, 
hydroxylamine oximation and 
acetic anhydride dehydration at the 7 site and introduction of amino groups at the 5 site through nitro groups or 
reductive amination are avoided, and 
heavy metals such as Pd / Pt / Zn and the like do not need to be used; the 
continuous operation of the whole steps is increased, the production cost of the 
silodosin intermediate is greatly reduced, and industrial large-scale production is facilitated.