Which of the following will best convert nitrobenzene into 3-fluorobromobenzene?
A
F2/AlCl3, Zn/HCl, NaNO2/HCl−0∘C, CuBr
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B
Br2/FeBr3, SnCl2/HCl, NaNO2/HBF4−0∘C, heat
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C
SnCl2/HCl, NaNO2/HBF4−0∘C, heat, Br2/FeBr3
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D
SnCl2/HCl, Br2/FeBr3, NaNO2/HBF4−0∘C, heat
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Solution
The correct option is DBr2/FeBr3, SnCl2/HCl, NaNO2/HBF4−0∘C, heat Nitrobenzene is brominated to form 1-bromo-3-nitrobenzene. Nitro group is then reduced to amino group to obtain 3-bromoaniline. The amino group is then diazotized and then replaced by F to obtain 1-bromo-3-fluorobenzene. Thus the reagents used are as given in option B.