834
Rao et al.
Table 2. Oxidative iodination of aromatic hydrocarbons
Conventional yield (%)
Sonication yield (%)
S. N
Substrate
Product
4-Iodo phenol
A
B
A
B
1
2
3
4
5
6
7
8
Phenol
64
62
69
70
65
69
67
70
69
68
65
69
67
68
69
69
55
69
66
68
66
68
69
65
65
69
68
70
68
62
64
70
67
68
59
68
66
69
66
66
66
66
67
69
68
68
66
69
65
65
66
69
55
66
69
60
62
60
68
70
67
70
67
69
70
65
70
66
69
66
60
69
o-Cresol
p-Cresol
m-Cresol
4-Chloro phenol
2-Chloro phenol
4-Bromo phenol
1,4 dihydroxy benzene
1-Naphthol
Benzaldehyde
1-(3-OH phenyl)ethanone
4-NO2 phenol
2-OH benzaldehyde
4-OH benzaldehyde
Toluene
2-OH-benzoic acid
2-OH-aniline
4-Iodo-2-methylphenol
2-Iodo-4-methylphenol
4-Iodo-3-methylphenol
4-Chloro-2-iodo phenol
2-Chloro-4-iodo phenol
4-Bromo-2-iodo phenol
2-Iodo benzene-1,4-diol
2-Iodo-1-naphthol
3-Iodobenz-aldehyde
1-(3-OH-4-Iodo phenyl)ethanone
4-NO2-2-iodo phenol
5-Iodo-2-OH-benzaldehyde
3-Iodo-2-OH-benzaldehyde
2-Iodo-toluene
3-Iodo-6-OH- benzoic acid
3-Iodo-4-OH-aniline
9
10
11
12
13
14
15
16
17
18
4-Cl-acetophenone
3-Iodo-4-Cl-acetophenone
Reaction time, conventional: 4–5 hr; sonication: 30–40 min; (A) KI/ IQCC; (B) KI / IQDC.
1
Each reaction is repeated at least half a dozen times and 7.2-Bromo-4-methylphenol: H NMR d 2.30 (s, 3H), 5.30 (s,
the reaction times are reproducible with an accuracy of §
5 min. The yields of the products have been compiled in
Tables 1 and 2.
1H, -OH), 6.79 (d, 1H, Ar-H), 7.01 (d, 1H, Ar-H), 7.25 (d,
1H, Ar-H); m/z D 187
1
8.4-Bromoaniline: H NMR d 3.70 (brs, 2H, -NH2), 6.54 (d,
2H, Ar-H), 7.24 (d, 2H, Ar-H); m/z D 172
1
9.2-Bromo-4-chloro phenol: H NMR d7.43 (d, 1H, Ar-H),
7.16 (dd, 1H, Ar-H), 6.94 (d, 1H, Ar-H), 5.49 (s, 1H,
Spectral Data of Certain Compounds
-OH); m/z D 207
1
1
10.1-Bromo 2-napthol: H NMR d5.10 (s, 1H, -OH), 6.6–8
1.4-Bromophenol: H NMR d 5.3 (s, 1H, -OH), 6.72(d, 2H,
(m, 6H, Ar-H); m/z D 223
Ar-H), 7.33 (d, 2H, Ar-H); m/z D 173
11.4-Iodo phenol : 1H NMR d D 7.48 (d, J D 7.98 Hz, Ar, 2H),
6.42 (d, J D 7.98 Hz,Ar,2H), 5.45 (br, s, -OH, 1H). (m/z D
220)
2.2-Bromo-4-nitrophenol: 1H NMR d6.16 (s, 1H, -OH), 7.8 (d,
1H, Ar-H), 8.07 (dd, 1H, Ar-H), 8.42 (d, 1H, Ar-H); m/z
D 218
1
3.2-Bromo-4-aminophenol: 1H NMR d 5.7 (s, 1H, -OH), 4.13
12.2-Iodo-1-naphthol: H NMR d 7.93 (d, 1H, 8-H), 7.69 (d,
)
2H, 4-H and 5-H), 7.46 (t, 1H, 7-H), 7.26 (t, 1H, 6-H),
7.15 (d, 1H, 3-H) 5.24 (s, 1H, OH); m/z:270
(s, 2H, -NH2 , 6.42–6.53 (m, 3H, Ar-H); m/z D 188
1
4.4-Bromoanisole: H NMR d 3.78 (s, 3H, -OCH3), 7.33 (d,
13.4-Iodo-anisole: 1H NMR d3.79 (s, 3H, -OMe), 6.66 (d, 2H,
Ar-H), 7.53 (d, 2H, Ar-H); m/z D 234
2H, Ar-H), 6.79 (d, 2H, Ar-H); m/z D 187
1
5.2-Bromo-4-methylanisole: H NMR d 2.27 (s, 3H, CH3),
14.4-Iodo toluene: 1H NMR d 2.3 (s, 3H, -Me), 6.9 (d, 2H, Ar-
H), 7.55 (d, 2H, Ar-H); m/z D 218
3.83 (s, 3H, -OCH3), 6.79 (d, 1H, Ar-H), 7.02 (dd, 1H, Ar-
H), 7.34 (d, 1H, Ar-H). m/z D 201
15.4-Iodo-3-methylphenol: 1H NMR d D 7.46 (d, J D 8.08 Hz,
Ar, 1H), 6.7 (s, Ar,1H), 6.38 (dd, J D 2.9,2.9 Hz, Ar, 1H),
2.35 (s, -CH3, 3H) 5.45 (br, s, -OH, 1H).). (m/z D 234
6.5-Bromo-2-hydroxy benzaldehyde: 1H NMR d 10.80 (s, 1H,
-OH), 9.83 (s, 1H, -CHO), 7.66 (d, 1H, Ar-H), 7.51 (dd,
1H, Ar-H), 6.64 (d, 1H, Ar-H); m/z D 201
Sch. 1. Where Y D OH, NH2 and NHCOCH3; X = electron donating or withdrawing group.