The flavor of beer can be tainted by a trace contaminant, called ortho-bromophenol. To reduce the incidents of contamination, beer manufacturers have used certified beer flavor standards to train professional beer tasters to recognize the flavor of ortho-bromophenol. Preparing these certified standards requires pure samples of ortho-bromophenol. Propose a synthesis of ortho-bromophenol starting from phenol. (Org. Synth. 1934, 14, 14.)
Choose from the reagents below.
A. dilute NaOH
B. conc. fuming, 1 mol H2SO4
C. HBr
D. Br2, FeBr3
E. Zn
F. Dilute H2SO4
G. HNO3
H. Hcl
I. Br2
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