Question

Propose a synthesis of triphenylmethanol, (C6H5)3COH, beginning with methyl benzoate, C6H5COOCH3, and bromobenzene, C6H5Br, via the intermediacy of an organometallic reagent.

Answer 1

Bromobenzene should be reacted as follows:

1. Mg(s) in THF

2. Methyl benzoate

3. H3O+

Step-by-step explanation:

First, bromobenzene reacts with magnesium in the solvent THF to form the organometallic intermediate phenylmagnesium bromide, which is a strong nucleophile. Two equivalents of reacts with methyl benzoate by nucleophilic attack at the carbonyl carbon to form triphenylmethoxide, which is then protonated in the final step to form the desired product triphenylmethanol.