[darkdevil]

Hi,
I wonder what method do you employ to substitute a secondary halogen with a hydrogen atom on a saturated alkyl chain? Is it dangerous to use a hydride source such as calcium hydride?

I need a convinient method to do so...
Will it be convinient if I convert the secondary halogen into a Grignard reagent and then just add water to yield my product?

Thanks!

[discodermolide]

You use tri-nbutyl tin hydride and AIBN in toluene and heat it. It forms tri-nbutyl tin chloride and the hydrogen ends up where the chlorine was.

[Dan]

The reaction is hydrogenolysis - this gives you a useful search term for google/textbook. There are several methods, some catalytic.

[stewie griffin]

The grignard came to my mind too (may have some competing beta hydride elimination since it's secondary, maybe not), though disco's recommendation is good too.
You could also try to reduce it off with superhydride (lithium triethylborohydride). I recall that'll open epoxides...I think it'll knock off halogens.