I would check the purity of the stannane, NMR works fine for it. If your bottle is old, get a new one its not that expensive.
Im not sure exactly about your procedure but I would use different base because BuLi can react with tributyltinCl to form tetrabutyl tin. Try LDA or tBuLi.
Quench the organoLi with water before TLC to get the dehalogenated aryl (if you have TLC of that) you can also use DMF to get the aldehyde and stain it with DMP.
Also, the reaction might need some time and temperature, maybe warm it to room temperature after the addition is complete. The organotin reagents are super nonpolar, be sure to check with suitable mobile phases (we used pure hexanes for that).
Maybe check this procedurehttp://orgsyn.org/demo.aspx?prep=CV8P0268