Pieces of 18 inch wide flashing installed prior to the brick work but on top of the house wrap in a stepped fashion periodically laying on top of the lapped upper portion of the siding to get the water back to the exterior of the wall is more along the lines that i would be thinking of.
Flashing a fieldstone chimney along siding.
Once the pan flashing is in place nail it to the roof sheathing and lay the shingles over the flashing.
Next comes the counterflashing.
Along the bend at both ends so that the flashing bends around the chimney at the bottom and overlaps at the ridge.
If this is running along the side of the house and not by the roof then maybe caulk at this point.
The other measures should have been taken before the siding was installed.
Sections of l shaped sheet metal are woven into the shingle courses and lapped up the side of the chimney.
The house will receive a cement style siding panel with no inside corner trim against the brick.
I ve looked around a bit and all the details i can find only deal with chimney roof flashing.
Yes you can caulk but in reality you should also be using chimney flashing which gets attached to and sealed to the chimney and then gets bent over the j channel.
Proper flashing around a chimney includes two layers.
On each end of the pan flashing cut about 1 1 2 in.
The first is called step flashing.