It is a separable problem. First you notice that the constant part of $f$ will play no role, since it would lead to a constant potential, so you may assume
$$
\int_0^{2\pi} f(\theta)d\theta =0.
$$
If you write
$$
f(\theta) = \sum_{n=1} a_n \cos n\theta + b_n\sin n\theta,
$$
then you notice that the solution $u$ can be written
$$
u(r,\theta) = \sum_{n=1} u_n(r)(a_n \cos n\theta + b_n\sin n\theta),
$$
where $u_n$ is a solution of
$$
\frac{1}{r} \left( r (1+\chi_[0,1/2]) u_n^\prime\right)^\prime - (1+\chi_[0,1/2])\frac{n^2}{r^2} u_n =0
$$
with the requirement that $u_n(0)$ is bounded and $u_n(1)=1$. This means in practice
$$
u_n = \begin{cases}\alpha_n r^n &\mbox{ for } 0\leq r\leq \frac12\\ \beta_n r^n + \gamma_n r^{-n} &\mbox{ for } \frac12 <r <1
\end{cases}
$$
together with continuity, $u_n(\frac 12 -) = u_n(\frac 12 +) $ and continuity of the flux $2 u_n^\prime (\frac 12 -) = u_n^\prime(\frac 12 +)$, and the final condition $u_n(1)=1$.
Three unknowns, three equations, you obtain a solution.
$$
a_n=\frac{2}{-3+4^{-n}},\quad b_n=\frac{3}{-3+4^{-n}},\quad c_n=\frac{1}{1-3\times4^{n}},
$$
in particular
$$
u_n^\prime(1)= n \frac{3+4^{-n}}{3-4^{-n}}
$$
And the normal flux at the boundary is
$$
\nabla u\cdot \nu (r=1) = \sum_{n=1}^\infty n \frac{3+4^{-n}}{3-4^{-n}} (a_n \cos n\theta + b_n\sin n\theta).
$$
This series will not always converge in the usual sense. For the problem to have a solution $u$ in $H^1$, $f$ must be such that
$$
\sum_{n=1}^\infty n (a_n^2 + b_n^2) <\infty
$$
which makes it $H^{1/2}(S_1)$. This is not enough for the flux to be well defined by the series above : each term is multiplied by $n$, so it is in $H^{-1/2}(S_1)$ : it only converges after an integration by parts against a series which is in $H^{1/2}(S_1)$. For the series to be convergent, you could impose for example
$$
\sum_{n=1}^\infty n (|a_n| + |b_n|) <\infty
$$
This is one of many approaches to this problem. Another popular one is to use layer potentials to solve this problem. In all cases, what you will notice is

- There is no silver bullet, giving you all you ever wanted to know about $\nabla u\cdot \nu $ in one simple formula.
- Different ways of representing the solution all have their uses. Just writing it as the flux on the boundary of the solution of that equation is the most convenient way to represent it for integrations by parts.
- The rate of convergence of the series depends completely on the regularity of $f$, which in turn decides of the rate of decay of the coefficients $a_n,b_n$.