For decades I dyed my chestnut brown hair . It's been all shades of chocolate, iced coffee, reddish brown, mahogany, titan red, auburn, dark blonde, platinum blonde and many others but not black.
I usually used Garnier Nutrisse permanent colour.
The thing is that it builds up into a block colour which is unnatural as normal hair is a melange of many tones, mostly unseen to the naked eye.
Last year I got fed up of the messing about with hair dyes and the 'block colour' effect so I went to a local multi-award winning salon and had a consultation. My hair is mostly grey except at the back from crown to make. She showed me what could be successfully achieved to lighten my hair in stages, from the deep reddish brown of home dyeing to a conker brown with subtle lighter flashes of copper on top and sides. There is a world of difference and I have the roots done every 5/6 weeks and flashes redone every 10 weeks besides having a complete re-style in the beginning.
I recommend going to a good salon and having a chat with their senior colourist.
They are the professionals who will know what can be achieved with your present colour and type of hair.
Good luck.