I’m working on a chemistry writing question and need an explanation and answer to help me learn.
References one relevant to the experiment and from JACS, ACIE, Org. Lett, or JOC. Specific comparisons are made between both the referenced methodologies and the method used in the experiment, focusing on the advantages/disadvantages of each method.
LITERATURE SEARCHFind one example in the primary literature published during the last two years year in which a
benzylic bromide is displaced by an oxygen nucleophile. Attach a printout of the article, with the relevant reaction(s) highlighted, to your report.
B.Reaction of Methyl (4-Bromomethylbenzoate with Phenol
To a 25-mL, round-bottomed flask equipped with a reflux condenser and a magnetic stir bar is added 0.92
mmol of phenol, 0.96 mmol of potassium carbonate, and 1.5 mL of acetone. The solution is heated to reflux
(Note 4). After 30 min of stirring at reflux, a solution of 0.873 mmol of 4-(bromomethyl)benzoate in 1.0
mL of acetone is added dropwise through the condenser while still heating. This solution is heated at reflux
for 1.5 h with stirring and then the solution is allowed to cool to room temperature.
ISOLATION AND PURIFICATION
The reaction mixture is quenched with 5.0 mL of sat. aq. ammonium chloride solution and the resulting
mixture is transferred to a 60-ml, separatory funnel containing 20 mL of EtOAc and 15 mL of water. The
layers are separated and the aqueous phase is extracted twice with 10-ml. portions of EtOAc. The combined
organic extracts are washed with 20 mL of water, 20 mL of brine, and are dried over magnesium sulfate.
The dried extracts are filtered through a glass filter frit and the filtrate is concentrated by rotary evaporation
to furnish a white solid (may remain as an oil, in which case recrystallization is not performed). The yield
(g) and melting point of the crude product are determined.
For recrystallization the following solvents are tested (Note 3):
bp 69 °C
bp 111 °C
bp 40 °C
The yield (g) and mp of the purified compound are determined. The IR (neat) and ‘H-NMR spectra of the
pure compound are recorded.
IR (neat) and ¹H-NMR (CDCI) spectra of the purified product are recorded
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1. After a short time, the color changes to red-orange.
2. The reaction mixture becomes colorless when complete. Work out a TLC analysis system
(hexane/EtOAc) with a little of the starting material while the reaction is running.
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