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Reaction with Diazonium Salts

Which of the ...

Question

Which of the following will best convert nitrobenzene into 3-fluorobromobenzene?

F_{2} / A l C l_{3}

Z n / H C l

N a N O_{2} / H C l - 0^{\circ} C

C u B r

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B r_{2} / F e B r_{3}

S n C l_{2} / H C l

N a N O_{2} / H B F_{4} - 0^{\circ} C

, heat

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S n C l_{2} / H C l

N a N O_{2} / H B F_{4} - 0^{\circ} C

, heat,

B r_{2} / F e B r_{3}

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S n C l_{2} / H C l

B r_{2} / F e B r_{3}

N a N O_{2} / H B F_{4} - 0^{\circ} C

, heat

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Solution

The correct option is D $B r_{2} / F e B r_{3}$ , $S n C l_{2} / H C l$ , $N a N O_{2} / H B F_{4} - 0^{\circ} C$ , 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.

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