Predicting the product of bromination of acetanilide
This is a classic $\alpha$-bromination of a carbonyl. You can achieve this with an electrophilic source of bromine like in the reaction conditions provided or something like N-bromosuccinimide.

The reason you're not getting the EAS product is because that's a much higher energy pathway since you need to temporarily break aromaticity. Given more time, heat, and bromine, you can probably get the ortho- and para- products, but you will still $\alpha$-brominate on the amide first.