The correct option is D before
When two sentences are combined with a conjunction, and one of them is dependent on the other for its full meaning, like "he goes to sleep" is dependent on the principal clause "Tim usually reads a novel", then the clause or sentence is subordinate and we use a subordinating conjunction. The given subordinate clause is time-related, as the events "reads a novel" and "goes to sleep" happen one after the other. 'Although' is a contrasting conjunction, and does not relate to time, hence option D is incorrect. 'Before' is a conjunction used for time-related sentences, and is appropriate here as Tim reads the book first, then after that he sleeps, hence option B is correct. 'So' is a conjunction that means 'for this reason, or therefore'. It's used when one of the sentences act as a reason or purpose. Tim reading a book is not the reason why he sleeps, hence 'so' is not used here, option A is incorrect. 'If' is a conjunction used when one of the sentences is a condition, on which the other sentence is based. None of the sentences here are conditional, and if 'if' is used, it means 'if he sleeps, he reads', which does not mean anything. Hence option B is incorrect.