For any $n\in\mathbb N$, let $A=\{x\in\mathbb N \mid 1 \leq x \leq n\}$ and $B=\{x\in\mathbb N \mid n+1 \leq x \leq 2n\}$.
Order the sets by greatest prime factor of each element, ascending. Let $A_1$ be the element in $A$ with the smallest gpf and $A_n$ be the largest, and likewise for $B$.
Conjecture: $\mathrm{gpf}(A_k)<\mathrm{gpf}(B_k)$ for all $1 \leq k \leq n$.
e.g. Let $n=5$, and we have:
$$ \begin{array}{|l|l|l|l|} \hline A_k&\mathrm{gpf}(A_k)&\mathrm{gpf}(B_k)&B_k\\ \hline 1&1&2&8=2^3\\ \hline 2&2&3&6=2\cdot 3\\ \hline 4&2&3&9=3^2\\ \hline 3&3&5&10=2\cdot 5\\ \hline 5&5&7&7 \\ \hline \end{array} $$
where $\mathrm{gpf}(B_k)$ is strictly greater than $\mathrm{gpf}(A_k)$.
I confirmed this empirically for $n<3000$. Informally, it looked like the trends strongly suggest it won't fail at any point.
If this is a known result or conjecture, please share. Otherwise, I'm looking for counterexamples or any advice on how a proof could be approached$-$or a reason why a proof is likely to be difficult or impossible, as seems more typical with this stuff.
Quicky data tables for $n<70$ are here.
This is a very interesting observation about the divisors of numbers. I have looked at it in a slightly different way from you and I believe there is good reason to think that not only is it true but that it becomes more and more 'obvious' as $n$ becomes large.
You have asked for any advice on how a proof could be approached. I think the following is a good way to go about this but it is not totally straightforward. Please feel free to ask if anything is unclear.
Let $p_i$ denote the $i$th prime. For any positive integer $n$, define $F(n,k)$ to be the number of positive integers less than or equal to $n$ which are divisible by no prime $p_i$, for $i>k$. Then your result depends on the following result.
Results for small $k$ such as $F(n,0)=1$ and $F(n,1)=t+1$, where $2^{t+1}>n\ge 2^t$, indicate why the Conjecture is likely to be true.
It may be possible to prove this conjecture by induction by using the following recurrence relation.
Proof This follows by considering separately those positive integers less than or equal to $n$ which are divisible by $p_k$ and those which are not.
The snag in using this result to obtain a rigorous proof of the Conjecture is that we can have $ \left \lfloor{\frac{2n}{{p_k}}}\right \rfloor= 2\left \lfloor{\frac{n}{{p_k}}}\right \rfloor+1$. However, I hope this will be of some use.