You need to write a schematic digram for your reaction equation to understand exactly what you want :)

MW it!

Use Appel reaction conditions: http://www.organic-chemistry.org/namedreactions/appel-reaction.shtm, but with the free alcohol.

Ray,

You may find Wang et al procedure better using ionic liquid

---Wang, Zhiming et al, Letters in Organic Chemistry, 4(1), 72-74; 2007.

Good luck

Thank you all for your contributions. I appreciate your time and input.

To a 50mL, three-necked flask equipped with a magnetic stirrer, dropping funnel and distilling apparatus, ionic liquid [emim]OTs (20 mL) and LiBr (4.1 g) were added and stirred at 80 °C. After 5 minutes, n-C6H13OTs (10 g, 0.04 mol) was added to the mixture by opening the dropping funnel.The reaction was followed by TLC. After the reaction, the product was distilled out of the reaction system under reducing pressure (Bp10 mmHg = 48-49 °C) and collected in a cooling trap (5.5 g, 85% yield).

---Wang, Zhiming et al, Letters in Organic Chemistry, 4(1), 72-74; 2007.

Clear

Tosylate is not the beast of leaving group (a bit overrated in my own opinion...). If you are stuck with it though, I would change acetone to NMP or DMAc. You can also use TBAB as the bromine source: using a more "naked" counterion tend to accelerate quite a bit those reactions. Alternatively, you can use sodium bromide and 18C6 as the crown ethers will trap the sodium inside, affording "naked" Br- in solution. As all the reagents involved are salts and solvents, Aq. qork-up or simply crash out the product from water (is solid) should be good enough for purification.

The apple reaction is a worthwhile try, although it can be tedious to remove the triphenylphosphine oxide. If your product is an oil, just swish it in heptane to remove the oxide.

@Pierre you comments are very insightful and Thank you for taking the time to respond.

 am planning on using catalytic 12-crown -4 ether which is specific for lithium ion as the source of bromine is LiBr . I am apprehensive of appel reaction atm as my product is soluble in hexane and I need to find useful protocols for effectively removing triphenylphophine. I am also going to try TBAB as my the source of my bromine ions if the crown ether strategy does not work out . 

I am not going to use NMP/DMAc as their boiling point is rather high (>200C) and am afraid I would have quite a hard time removing it if I use it as a solvent . I am curious as to how you can effectively remove NMP/DMAc other than either using a rotovap at a really high setting or using a powerful lypholizer ? You mentioned you are not fond of tosylate group as a leaving group. What is in your opinion a better leaving group for bromination/iodination reactions?

NMP/DMAc/DMF are most often removed by extraction (thy will go in the aq. phase). You might have some residual solvent if you extreact with ethyl acetate, but in your case since the product is soluble in hexane, you could extract with hexane or diethyl ether and it should remove pretty much all of your reaction solvent. If your product is a solid, you can also just add water to your reaction mixture and filter the solid. I use this type of "work-up/purification" quite often, especially when my product is the only organic solid used in the reaction. Just be careful to add the water slowly to form a fine precipitate or else the product might just form a gum...

I rather avoid Sn2 all together actually...If I have to, I prefer mesylate than tosylate, or I will make the bromide through an apple reaction. In your case, if your product is soluble in hexane, it's ideal as the triphenyl phosphine oxide is not. You can then remove most of it by trituration prior to flash chromatography (wathever's left should separate well if there is only a small amount).

Also, I don't know what you plan to do with this alkyl bromide, but the tosylate might be as effective than the bromide, especially if your conversion is a 50% yield...You might get a better overall yield by simply forming the mesylate up front and using it directly in your alkylation step (I presume the bromide was meant to be alkylated through SN2...).

Best of luck

@ Pierre . Thank you for all your time and advice. I was able to increase my yield using 12-crown-4 ether. I am in the process of fine tuning my procedure . 

To convert tosylate to bromine first hydrolyse  tosylate to alcohol then brominate alcohol by PBr3 or by heating with KBr & Conc. H2SO4. Another way to reduce tosylate by LiAlH4 to alkyl group & carry out bromination by N-bromo succinimide if it is in allylic position.