I'd like to sum up some specific parts of Wojowu's answer:
The smallest odd $n$ with $\varphi(n)/n = \prod_{p|n}(1-1/p) \leq 1/2$ is $105 = 3\cdot 5\cdot 7$
$\varphi(n)/n < 1/2$ also for
- $3 \cdot 5 \cdot p \cdot q$ with $7 \leq p \leq 13$ prime and $q\in\mathbb{N}^+$ odd
The smallest odd $n$ with $\varphi(n)/n \leq 1/2$ not found yet is $3003 = 3\cdot 7 \cdot 11 \cdot 13$
$\varphi(n)/n < 1/2$ also for
$3 \cdot 7 \cdot 11 \cdot p \cdot q$ with $13 \leq p \leq 19$$13 \leq p \leq 23$ prime and $q\in\mathbb{N}^+$ odd
$3 \cdot 7 \cdot 13 \cdot p \cdot q$ with $17 \leq p \leq 23$$17 \leq p \leq 19$ prime and $q\in\mathbb{N}^+$ odd
The natural question then is: What comes next, what is the smallest $n$ with $\varphi(n)/n \leq 1/2$ not found yet? And so on, and so on. (I have to admit, @Wojowu, that I'm still not able to answer this.)
Some shortest sequences of primes $p_1,\dots,p_k$ with $\prod_{p_i}(1-1/p_i) \leq 1/2$ and their products:
- $3\cdot 11 \cdot 13 \cdot 17 \cdot 19 = 138,567$ (is this the next one?)
- $3 \cdot 13 \cdot 17 \cdot 19 \cdot 23 \cdot 29 \cdot 31 = 260,468,169$
- $5\cdot 7 \cdot 11 \cdot 13 \cdot 17 \cdot 19 \cdot 23 = 37,182,145$