How tall is he? How much does he weigh?
Several of my DD's friends (oldest turned five in December) are in boosters, although they're a lot bigger than her (she's just 40 inches, and 34 lbs). That being said, there are several of them, DD included, who are still in 5 pt harnesses.
I think your biggest problem would be the desirability of moving to the booster. I couldn't move DD to the booster in one car, because she'd want it in all cars. It's all or nothing for us. (We are lucky, though, to have 3 seats for her, one in my car, one in DH's, and one in my mom's.)