Page 1058 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1034 Scheme 11.6. (Continued)

CHAPTER 11 11 k
RONO
Aromatic Substitution CH NH CH Br
Reactions 3 2 CuBr 3
2
76%
NaOAc,
12 l + 18-crown-6
BF – Br
N 2
4
BrCCl 3 88%
Cl Cl
13 m Br
Br 1) HONO
I 72–83%
2) KI
NH 2
Br
14 n
Br 1) HONO F
NH 2 2) HPF 6
3) Δ 73–75%
15 o 1) HONO F F
H N NH 2) HBF
2 2 4
3) Δ 54–56%
16 p OCH
2
O 3 NO 2 1) SnCl , DMF
O H ONO, BF
2) t-C 4 9 3
NO 2
H 3) CuCl, CuCl , CCl
O O H 2 4
N N
CH O C N N NHCO CH CH CH 2
2
2
3 2 OCH 3 Cl
O O O
H H O
Cl
O H O H
OCH
3 N N
CH O C N N NHCO CH CH CH 2
3
2
2
2
O O
H H
D. Replacement by other anions OCH 3
C N
17 q NH
2 1) HONO CH 3
CH 3
2) CuCN 64–70%
18 r
1) HONO
2) NaN
NH 2 3 N 3 88%
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