Hello, I am trying to the do bromination of a bulky secondary alcohol using P Br3 and the solvent used for the reaction is diethyl ether. When I do a TLC of the reaction after 15 mins of addition of PBr3, I see almost complete conversion and see the dense spot of the product. However once i do work-up and take TLC of the organic layer my product is lost and the starting material is now visible again.

Similarly when i load the reaction mixture directly on the flash column. still my product is lost and it is brocken back to the starting material.