The Brook rearrangement in organic chemistry is a rearrangement reaction in which a organosilyl group switches position with a hydroxyl proton over a carbon to oxygen covalent bond under the influence of a base. It is named for the Canadian chemist Adrian Gibbs Brook (b. 1924). The reaction product is a silyl ether.
The silyl substituents can be aliphatic (methyl) or aromatic (phenyl) and the alcohol is secondary or tertiary with aliphatic or aryl groups. The base is an amine, sodium hydroxide, an organolithium reagent or an alkali metal alloy such as Na/K. When the reactant is a silylmethanol the reaction is a 1,2-brook rearrangement but rearrangements over larger carbon skeletons are also possible.
Read more about Brook Rearrangement: Reaction Mechanism, Scope
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“The only house
Beyond where they were was a shattered seedpod.
And below roared a brook hidden in trees,
The sound of which was silence for the place.”
—Robert Frost (1874–1963)