Yeah you tell him there is a 3 headed monkey and as you creep up he turns around and tells you to back off.
It has to be a glitch since you back off, plus once Guybrush pulls out the Bottle Breaker there is a Bottle Breakder still sitting on top of the box in it's place.
Balin2k also said:
yeah i got that when i used the bottle on the breaker and was like huh? guybrush had it in his hand but it was still on the table also. im guessing a glitch. and me being me went back to my last save game and did the puzzle properly. to mrsbbc na i didnt see it in my inverntory. deffo a glitch
So it seems like there is a glitch since he reloaded the game and did the puzzle the right way.