What is the reason for the time outs he does get?
I would try just sending him off. "oh, you are not playing nicely you need to leave the block area" "oh, you threw the book, you need to choose a new area to play in you cannot stay in the book area when you behave that way". His punishment is just not being allowed to continue doing what he was doing. "If you can't keep your hands to yourself you will have to go play on your own". I find giving this type of warning when you sense things are about to go amiss not only give them the chance to change their behavior...but gives them the ownership when you then remove them a minute later because they didn't change their behavior. "You didn't keep your hands to yourself so now you have to go play by yourself like I just warned you".
If the child very rarely gets in trouble then it can be really distressing when they are corrected for bad behavior. It means a lot more to them than the child that is constantly being in trouble. The time out may just be too severe/hard a punishment for him emotionally. He still needs to have consequences but something that he learns from but doesn't escalate the issues to an extreme with benefit everyone (especially you).
My daughter would so not handle a time out on a chair. She is sent to her bed. Her bed is her safe zone, it has her special bears and blankies. She goes up losing it and bawling her head off...and this continues for a bit but when she is ready to calm herself she has her special things and she has her space to decompress. Then I go in and set her free. It isn't really a "time out" but removing her from the situation due to her behavior until she is ready to come back and try again. No audience also helps end things quickly for her!

































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