Triton B-mediated efficient and convenient alkoxylation of activated aryl and heteroaryl halides

Article abstract of DOI:10.1080/00397910903219518

A simple and convenient one-pot synthesis of aryl alkyl ethers by the alkoxylation of aryl halides with alcohol in the presence of Triton B as a base is described. The procedure is applicable for a variety of aryl and heteroaryl halides, and yields are very good. The use of a nonmetallic base and solvent-free conditions are important features of the reaction. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/00397910903219518

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Triton B–Mediated Efficient and
Convenient Alkoxylation of Activated
Aryl and Heteroaryl Halides
H. M. Meshram a , P. Ramesh Goud a , B. Chennakesava Reddy a & D.
Aravind Kumar a
a Organic Chemistry Division I, Indian Institute of Chemical
Technology, Hyderabad, India
Version of record first published: 17 Jun 2010.
To cite this article: H. M. Meshram, P. Ramesh Goud, B. Chennakesava Reddy & D. Aravind Kumar
(2010): Triton B–Mediated Efficient and Convenient Alkoxylation of Activated Aryl and Heteroaryl
Halides, Synthetic Communications: An International Journal for Rapid Communication of Synthetic
Organic Chemistry, 40:14, 2122-2129
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Synthetic Communications1, 40: 2122–2129, 2010
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397910903219518
TRITON B–MEDIATED EFFICIENT AND CONVENIENT
ALKOXYLATION OF ACTIVATED ARYL AND
HETEROARYL HALIDES
H. M. Meshram, P. Ramesh Goud, B. Chennakesava Reddy,
and D. Aravind Kumar
Organic Chemistry Division I, Indian Institute of Chemical Technology,
Hyderabad, India
A simple and convenient one-pot synthesis of aryl alkyl ethers by the alkoxylation of aryl
halides with alcohol in the presence of Triton B as a base is described. The procedure is
applicable for a variety of aryl and heteroaryl halides, and yields are very good. The use
of a nonmetallic base and solvent-free conditions are important features of the reaction.
Keywords: Alkoxylation; aryl halides; ethers; Triton B
Aryl alkyl ethers form the core structures of many natural products and serve as
intermediates for the preparation of dyes, plant-protection agents, fragrances, and
end products in agriculture and the pharmaceutical industry.[1] Ethers are also used
as phenol precursors, which in turn are versatile intermediates for the preparation
of oxygenated heterocycles.[2] There are numerous methods for the synthesis of
ethers. Among these, the Ullmann coupling[3] is a straightforward method for ether
formation. However, this method has limited utility because of high temperatures
(200 ꢀC), the use of high-boiling solvents, and the sensitivity of other functional group
at high temperatures. Some of the methods[4] use alkylating phenols with alkyl
halides or alkyl sulfates, which are very toxic and release acid. A green version of
the Williamson ether synthesis, using weak alkylation agents, has been reported.[1]
Recently, catalytic methods[5] have been developed to increase the efficiency of the
reaction in mild conditions. Parrish and Buchwald[6] reported the synthesis of ethers
from aryl halides and butoxide in the presence of Pd catalyst and ligand. Another
method[7] demonstrated the synthesis of ether from aryl halides using Pd catalyst
via the formation of phenoxide, followed by the addition of alkyl iodide. Zinc was
also found to catalyze ether formation under microwave irradiation in dimethylfor-
mamide (DMF) in the absence of a base.[8] However, MeOH as alkylation reagent
has been reported at very high temperature (250 ꢀC), which leads to C-alkylation as
side reaction.[9] Most commonly, the ethers are prepared by the alkylation of phenol
Received May 4, 2009.
Address correspondence to H. M. Meshram, Organic Chemistry Division I, Indian Institute of
Chemical Technology, Hyderabad 500 007, India. E-mail: hmmeshram@yahoo.com
2122

CONVENIENT SYNTHESIS OF ARYL ALKYL ETHERS
2123
with alkyl halides, but this method has limitations because of instability, low vapor
pressure, and the toxic nature of alkyl halides. Moreover, some of the methods suffer
from certain drawbacks such as use of expensive catalyst or ligand and an inert
atmosphere. In addition, the contamination of metal ions in the product may
pose environmental concerns.[10] Though few procedures provide ligand-free
conditions,[11] the use of a copper catalyst generates copper salt as a by-product.
So, it remains a challenge to develop an aryl alkyl ether synthesis from aryl halides
and alcohols that would not require a ligand, Pd catalyst, or copper salt. Recently,
Triton B has become more popular because of its efficiency and nonmetallic nature.
It has been successfully employed for Michael addition,[12] nitro-aldol conden-
sation,[13] and carbamate formation reactions.[14] However, there is no report of aryl
alkyl ether formation using a nonmetallic base. In continuation of our work in the
development of nonmetallic reagents,[15] herein we report aryl alkyl ether formation
by the alkoxylation of active aryl halides with alcohol in the presence of Triton B
as a base (Scheme 1).
When the reaction of 4-fluoro nitrobenzene (1 equiv.) and Triton B (1.1 equiv.
40% methanolic solution) was carried out at rt, the reaction remained incomplete
after 3 hr. To increase the efficiency of the reaction, we have performed the reaction
with 3 equiv. of Triton B (40% methanolic solution), and to our surprise, the reaction
proceeded efficiently and completed in 10 min at rt. After workup, the product,
4-nitrophenyl methyl ether, was isolated in good yield (95%). The formation of
methyl ether indicated that methoxide ions are generated from methanol. This
protocol was extended to other alcohols to obtain a variety of ethers. We presume
that reaction may proceed via nucleophilic substitution. Initially, the alkoxide may
be formed, and then nucleophilic displacement of aryl halide occurs (Table 1).
First, we concentrated our study on making the protocol more general by
examining the substrates with different electron-withdrawing groups. For example,
2-methyl-4-nitro fluorobenzene (entry 1) and 2-methyl-4-nitro chlorobenzene (entry
3) reacted smoothly with alcohols (a–f) to give excellent yields of aryl alkyl ethers,
which are comparable to those obtained using ligand and copper catalysts.[16] During
the investigation, it was noticed that the electron-donating system suppresses the
reaction whereas the electron-withdrawing substituent facilitates the reaction. Next,
we examined the effect of other electron-withdrawing groups for alkoxylation. Thus,
2,8-bis (trifluoromethyl)-4-iodo quinoline (entry 4) reacted rapidly with Triton B to
Scheme 1. Triton B–mediated efficient and convenient alkoxylation of activated aryl=hetero aryl halides.

2124
H. M. MESHRAM ET AL.
Table 1. Synthesis of aryl alkyl ethersa from aryl halides
Reaction
condition
Time
(min)
Entry
1
Aryl halides
Alcohols
a) CH3OH
Product
Yieldb
1a
1b
1c
rt
15
30
40
93
90
89
b) CH3CH2OH
c) CH3CH2CH2OH
d)
50
50
1d
1e
1f
70
70
70
60
60
70
87
85
81
e)
f)
2
3
4
5
a) CH3OH
2a
2b
2c
rt
10
20
30
95
93
91
b) CH3CH2OH
c) CH3CH2CH2OH
d)
50
50
2d
2e
2f
70
70
70
45
55
60
89
88
85
e)
f)
a) CH3OH
3a
3b
3c
rt
15
35
50
93
89
84
b) CH3CH2OH
c) CH3CH2CH2OH
d)
50
50
3d
3e
3f
70
70
70
65
60
70
80
78
75
e)
f)
a) CH3OH
4a
4b
4c
rt
05
20
35
93
91
89
b) CH3CH2OH
c) CH3CH2CH2OH
d)
50
50
4d
4e
4f
70
70
70
45
50
60
85
83
81
e)
f)
a) CH3OH
b) CH3CH2OH
c) CH3CH2CH2OH
5a
5b
5c
rt
15
25
40
88
85
84
50
50
d)
e)
f)
5d
5e
5f
70
70
70
50
60
70
81
79
75
6
a) CH3OH
6a
6b
6c
rt
05
15
15
95
90
89
b) CH3CH2OH
c) CH3CH2CH2OH
d)
50
50
6d
6e
6f
70
70
70
30
35
50
86
84
81
e)
f)
7
a) CH3OH
b) CH3CH2OH
c) CH3CH2CH2OH
7a
7b
7c
rt
15
30
45
93
89
87
50
50
d)
7d
70
60
83
(Continued )

CONVENIENT SYNTHESIS OF ARYL ALKYL ETHERS
2125
Table 1. Continued
Reaction
condition
Time
(min)
Entry
8
Aryl halides
Alcohols
a) CH3OH
Product
Yieldb
8a
8b
8c
rt
10
20
30
91
88
85
b) CH3CH2OH
c) CH3CH2CH2OH
d)
50
50
8d
9a
70
rt
45
15
81
87
9
10
11
a) CH3OH
b) CH3CH2OH
c) CH3CH2CH2OH
d)
9b
9c
50
50
25
40
82
81
9d
10a
70
rt
50
20
78
86
a) CH3OH
b) CH3CH2OH
c) CH3CH2CH2OH
d)
10b
10c
50
50
40
55
84
80
10d
11a
70
rt
65
25
76
82
a) CH3OH
b) CH3CH2OH
c) CH3CH2CH2OH
d)
11b
11c
11d
50
50
70
45
60
70
81
78
72
aAll products exhibited physical and spectral (NMR, mass, IR) properties in accordance with their
assigned structures.
bIsolated yield.
afford a good yield of expected methyl ethers. This may be because of the strong
electron-withdrawing effect of the –CF3 group. The aryl halides bearing a carbonyl
or a cyano group also successfully underwent the alkoxylation with different alco-
hols (a–e). 4-Fluoroacetophenone (entry 10) and 4-fluorobenzaldehyde (entry 9)
reacted with aliphatic alcohols (a–d) and led to corresponding ethers in good yields.
o-Fluorobenzonitrile (entry 11) also gave analogous results with alcohols. Alkoxyla-
tion of 4,40-difluoro benzophenone (1 equiv) with methanolic Triton B (1 equiv) gave
a mixture of monomethoxy and dimethoxy benzophenone products, while the use of
2 equiv. of Triton B resulted in the formation of only 4,40-dimethoxy benzophenone.
Further, we studied the reaction of different alcohols as alkoxylating reagents.
The reaction of Triton B was very fast, but as the number of carbons increases (alco-
hols a–c), heating was necessary for optimum conversion. Allylic and propargylic
alcohol required higher temperatures for completion of the reactions. However,
the aryl halides bearing carbonyl and nitrile groups (entries 7–10) were not reacted
with allylic and propargyl alcohol. The substrates bearing nitro and two different
halogens were studied to show the selectivity among halogens. Thus, in the reaction
of 2-bromo-5-chloro nitrobenzene (entry 5) with Triton B (40% methanolic solution)
at rt, the bromo reacted selectively to afford 4-chloro-2-nitroanisole in good yield.
As expected, the formation of dimethoxy product was not observed because once
one halogen reacts, the formed methoxy group would suppress the reactivity of
system. Many pharmaceutical products contain aliphatic alkoxy groups; in this
context, the present protocol may be an attractive alternate for the preparation of
alkoxyl aryl ethers. The additional advantage of the present reaction is that it
avoids any metal contamination in the pharmaceutical products. Moreover, the

2126
H. M. MESHRAM ET AL.
present method uses alcohols that are stable and easily available. It is worth
mentioning that the method tolerates the presence of aldehyde and nitrile function-
ality. In addition, double and triple bonds remain unaffected in the same reaction
conditions.
In conclusion, we demonstrate a one-pot method for alkoxylation of aryl and
heteroaryl halides with lower alcohols in the presence of Triton B. This protocol
avoids the use of lachrymatric alkyl halides and Pd complexes or ligands. Generality
toward a variety of aryl halides and the nonmetallic nature of the base makes this
protocol an ecofriendly alternative.
EXPERIMENTAL
General
All reactions were carried out without any special precautions in an
atmosphere of air. Chemicals were purchased from Fluka and S. D. Fine Chemicals.
Thin-layer chromatography (TLC) used precoated silica gel plates (60 F254, 0.2-mm
1
layer; E. Merck). H NMR spectra were measured on a Varian 200 or Bruker 300
spectrometer in CDCl3; d in parts per million and J in hertz. Mass spectra were
measured on a VG Autospec in m=z.
Experimental Procedure
Triton B (1.5 equiv., after removing of methanol) was dissolved in alcohol (1.1
equiv.) and stirred for 10 min. Then, aryl halide (1 equiv.) was added slowly with
stirring, and the reaction continued for the stipulated time period (see Table 1). After
completion of reaction as indicated by TLC, excess alcohol was removed under
reduced pressure, and the residue was diluted with water. It was extracted with ethyl
acetate, the organic layer washed with water and dried over Na2SO4, and the solvent
was removed under reduced pressure. The crude product was purified through a
column (hexane–EtoAc) to give the pure product.
Characteristic Data of Some Representative Compounds
Compounds 1a and 3a. Solid; mp 50–51 ꢀC; 1H NMR (200 MHz, CDCl3): d
(ppm) 2.26 (s, 3H), 3.92–3.94 (m, 3H), 6.81 (d, 1H, J ¼ 7.0 Hz), 8.02 (d, 1H,
J ¼ 2.5 Hz), 8.10 (dd, 1H, J ¼ 2.5 Hz, J ¼ 9.0 Hz); FABMS: m=z 168 (Mþ þ 1). IR
(KBr) n ¼ 1610, 1592, 1510, 1498, 1260, 1100, 1020 cmꢁ1. Anal. calcd. for
C8H9NO3: C, 57.48; H, 5.43; N, 8.38. Found: C, 57.43; H, 5.40; N, 8.39.
1
Compounds 1b and 3b. White solid; mp 66–68 ꢀC; H NMR (200 MHz,
CDCl3): d (ppm) 1.5 (t, 3H, J ¼ 7.0 Hz), 2.3 (s, 3H), 4.1 (q, 2H, J ¼ 7.0 Hz), 6.85
(d, 1H, J ¼ 8.5 Hz), 8.0 (s, 1H), 8.1–8.2 (m, 1H); FABMS: m=z 181 (Mþ). IR
(KBr) n ¼ 2921, 2855, 1510, 1345, 1257 cmꢁ1. Anal. calcd. for C9H11NO3: C,
59.66; H, 6.12; N, 7.73. Found: C, 59.68; H, 6.10; N, 7.79.
1
Compounds 1d and 3d. Yellowish red liquid; H NMR (200 MHz, CDCl3):
d (ppm) 1.45 (d, 6H, J ¼ 6.0 Hz), 2.25 (s, 3H), 4.6–4.8 (m, 1H), 6.85 (d, 1H,

CONVENIENT SYNTHESIS OF ARYL ALKYL ETHERS
2127
J ¼ 9.0 Hz), 8.02 (m, 1H), 8.1 (m, 1H); FABMS: m=z 195 (Mþ). IR (KBr) n ¼ 3005,
2927, 1540, 1240 cmꢁ1. Anal. calcd. for C10H13NO3: C, 61.53; H, 6.71; N, 7.17.
Found: C, 61.43; H, 6.60; N, 7.19.
Compounds 1e and 3e. Semisolid; 1H NMR (200 MHz, CDCl3): d (ppm) 1.8
(s, 3H), 4.6 (s, 2H), 5.1 (s, 1H), 5.2 (s, 1H), 6.8 (d, 1H, J ¼ 8.5 Hz), 7.9 (s, 1H),
8.1–8.15 (m, 1H); FABMS: m=z 230 (Mþ Na), 207 (Mþ). IR (KBr) n ¼ 2922,
2852, 1591, 1514, 1341, 1259 cmꢁ1. Anal. calcd. for C11H13NO3: C, 63.76; H, 6.32;
N, 6.76. Found: C, 63.78; H, 6.34; N, 6.74.
1
Compound 2a. White solid; mp 52–53 ꢀC; H NMR (200 MHz, CDCl3): d
(ppm) 3.9 (s, 3H), 6.9 (d, 2H, J ¼ 9.0 Hz), 8.2 (d, 2H, J ¼ 9.0 Hz); FABMS: m=z
176 (Mþ Na), 132. IR (KBr) n ¼ 3031, 1535, 1256 cmꢁ1. Anal. calcd. for
C7H7NO3: C, 54.90; H, 4.61; N, 9.15. Found: C, 54.92; H, 4.65; N, 9.19.
1
Compound 2f. White solid; mp 112–114 ꢀC; H NMR (200 MHz, CDCl3): d
(ppm) 2.5 (s, 1H), 4.8 (s, 2H), 7.05 (d, 2H, J ¼ 9.0 Hz), 8.25 (d, 2H, J ¼ 9.0 Hz);
FABMS: m=z 178 (Mþ 1), 177 (Mþ). IR (KBr) n ¼ 3111, 2925, 2123, 1493, 1332,
1174 cmꢁ1. Anal. calcd. for C9H7NO3: C, 61.02; H, 3.98; N, 7.91. Found: C,
61.12; H, 3.94; N, 7.89.
1
Compound 4a. White solid; mp 85–88 ꢀC; H NMR (200 MHz, CDCl3): d
(ppm) 4.1 (s, 3H), 7.1 (s, 1H), 7.65 (t, 1H, J ¼ 8.0 & 7.3 Hz), 8.1 (d, 1H, J ¼ 7.3 Hz),
8.4 (d, 1H, J ¼ 8.0 Hz); FABMS: m=z 296 (Mþ 1), 295 (Mþ), 177; IR (KBr):
n ¼ 3050, 3012, 2928, 1579, 1498, 1237 cmꢁ1. Anal. calcd. for C12H7F6NO: C,
46.02; H, 2.90; F, 36.40; N, 4.47. Found: C, 44.08; H, 2.96; F, 36.44; N, 4.43.
Compound 4e. Light yellow solid; mp 72–73 ꢀC; 1H NMR (200 MHz,
CDCl3): d (ppm) 1.8 (s, 3H), 4.8 (s, 2H), 5.1 (s, 1H), 5.2 (s, 1H), 7.1 (s, 1H), 7.6
(t, 1H, J ¼ 6.6 Hz, J ¼ 8.0 Hz), 8.1 (d, 1H, J ¼ 6.6 Hz), 8.5 (d, 1H, J ¼ 8.0 Hz);
FABMS: m=z 335 (Mþ). IR (KBr): n ¼ 3057, 2970, 1598, 1476, 1220 cmꢁ1. Anal.
calcd. for C15H11F6NO: C, 53.74; H, 3.31; F, 34.00; N, 4.18. Found: C, 53.70; H,
3.34; F, 34.08; N, 4.20.
Compound 5a. Light yellow solid; mp 93–95 ꢀC; 1H NMR (200 MHz,
CDCl3): d (ppm) 3.9 (s, 3H), 7.2 (s, 1H), 7.65–7.70 (m, 1H), 7.8–7.9 (m, 1H);
FABMS: m=z 188 (Mþ 1), 187 (Mþ). IR (KBr): n ¼ 2998, 2926, 1570, 1255 cmꢁ1
.
Anal. calcd. for C7H8ClNO3: C, 44.82; H, 3.22; Cl, 18.90; N, 7.47. Found: C,
44.88; H, 3.20; Cl, 18.80; N, 7.50.
Compound 6a. White floppy solid; mp 106–108 ꢀC; 1H NMR (200 MHz,
CDCl3): d (ppm) 4.05 (s, 3H), 6.9 (d, 1H, J ¼ 9.1 Hz), 8.4 (dd, 1H, J ¼ 3.0 Hz),
9.05 (d, 1H, J ¼ 3.0 Hz); FABMS: m=z 154 (Mþ). IR (KBr): n ¼ 3007, 2967, 1591,
1482, 1260 cmꢁ1. Anal. calcd. for C6H6N2O3: C, 46.76; H, 3.92; N, 18.18. Found:
C, 46.70; H, 3.98; N, 18.14.
Compound 6d. Pale yellow solid; mp 52–53 ꢀC; 1H NMR (200 MHz, CDCl3):
d (ppm) 1.38 (d, 6H, J ¼ 6.2 Hz), 5.43 (heptet, 1H, J ¼ 6.2 Hz), 6.74 (d, 1H,
J ¼ 9.1 Hz), 8.33 (dd, 1H, J ¼ 2.8 Hz, J ¼ 9.1 Hz), 9.07 (d, 1H, J ¼ 2.8 Hz); FABMS:
m=z 183 (Mþ 1), 182 (Mþ), 167, 140. IR (KBr): n ¼ 3170, 3090, 3070, 2970, 1695,

2128
H. M. MESHRAM ET AL.
1510, 1470, 1310, 1265 cmꢁ1. Anal. calcd. for C8H10N2O3: C, 52.74; H, 5.53; N,
15.38. Found: C, 52.70; H, 5.50; N, 15.39.
Compound 6f. Yellow solid; mp 149–150 ꢀC; 1H NMR (200 MHz, CDCl3): d
(ppm) 2.5 (s, 1H), 5.2 (s, 2H), 7.4 (s, 1H), 8.1 (d, 1H, J ¼ 2.9 Hz), 8.5 (d, 1H,
J ¼ 2.9 Hz); FABMS: m=z 178 (Mþ), 176, 175, 163. IR (KBr): n ¼ 3111, 2925,
2123, 1589, 1493, 1332, 1247 cmꢁ1. Anal. calcd. for C8H6N2O3: C, 53.94; H, 3.39;
N, 15.72. Found: C, 53.97; H, 3.40; N, 15.79.
Compound 8a. White solid; mp 146 ꢀC; 1H NMR (200 MHz, CDCl3): d
(ppm) 3.85 (s, 6H), 6.9 (d, 4H, J ¼ 8.8 Hz), 7.9 (d, 4H, J ¼ 8.8 Hz); FABMS: m=z
265 (Mþ Na) . IR (KBr): n ¼ 3067, 3017, 2921, 1640, 1598, 1256 cmꢁ1. Anal. calcd.
for C15H14O3: C, 74.36; H, 5.82; Found: C, 74.40; H, 5.80.
1
Compound 9a. Brown liquid; H NMR (200 MHz, CDCl3): d (ppm) 3.9 (s,
3H), 7.0 (d, 2H, J ¼ 8.5 Hz), 7.8 (d, 2H, J ¼ 8.5 Hz), 9.87 (s, 1H); FABMS: m=z
175 (Mþ K), 135 (M ꢁ 1þ). IR (KBr): n ¼ 2924, 2854, 1741, 1602, 1255 cmꢁ1. Anal.
calcd. for C8H8O2: C, 70.58; H, 5.93. Found: C, 70.53; H, 5.90.
1
Compound 9b. Liquid; H NMR (200 MHz, CDCl3): d (ppm) 1.38 (t, 3H,
J ¼ 6.0 Hz), 4.15 (q, 2H, J ¼ 6.0 Hz), 7.13 (d, 2H, J ¼ 12.0 Hz), 7.88 (d, 2H,
J ¼ 12.0 Hz); FABMS: m=z 150 (Mþ). IR (KBr): n ¼ 2934, 2844, 1731, 1600,
1255 cmꢁ1. Anal. calcd. for C9H10O2: C, 71.98; H, 6.71. Found: C, 71.93; H, 6.70.
1
Compound 9d. Pale yellow liquid; H NMR (200 MHz, CDCl3): d (ppm)
1.06 (t, 3H, J ¼ 7.6 Hz), 1.80–1.87 (m, 2H), 4.0 (t, 2H, J ¼ 6.6 Hz), 7.0 (d, 2H,
J ¼ 8.8 Hz), 7.83 (d, 2H, J ¼ 8.8 Hz), 9.88 (s, 1H); FABMS: m=z 164 (Mþ). IR
(KBr): n ¼ 2944, 2864, 1745, 1602, 1250 cmꢁ1. Anal. calcd. for C10H12O2: C, 73.15;
H, 7.37. Found: C, 73.13; H, 7.40.
1
Compound 10a. Semisolid; H NMR (200 MHz, CDCl3): d (ppm) 2.53 (s,
3H), 3.86 (s, 3H), 6.89 (d, 2H, J ¼ 9.0 Hz), 7.89 (d, 2H, J ¼ 9.0 Hz); FABMS: m=z
173 (Mþ Na), 135; IR (KBr) n ¼ 3005, 2963, 2842, 1675, 1601, 1256 cmꢁ1. Anal.
calcd. for C9H10O2: C, 71.98; H, 6.71. Found: C, 71.94; H, 6.70.
1
Compound 10b. Semisolid; H NMR (200 MHz, CDCl3): d (ppm) 1.3 (t,
3H), 2.6 (s, 3H), 4.0 (q, 2H), 6.9 (d, 2H, J ¼ 8.9 Hz), 7.9 (d, 2H, J ¼ 8.9 Hz); FABMS:
m=z 187 (Mþ Na), 149; IR (KBr) n ¼ 3005, 2963, 2842, 1675, 1601, 1256 cmꢁ1. Anal.
calcd. for C10H12O2: C, 73.15; H, 7.37. Found: C, 73.14; H, 7.40.
1
Compound 11d. Liquid; H NMR (200 MHz, CDCl3): (ppm) 1.39 (d, 6H,
J ¼ 6.1 Hz), 4.64–4.65 (m, 1H), 6.91–6.98 (m, 2H), 7.45–7.57 (m, 2H); FABMS:
m=z 161 (Mþ 1), 119, 91, 64. IR (KBr): n ¼ 2924, 2854, 2224, 1602, 1255 cmꢁ1. Anal.
calcd. for C10H11NO: C, 74.51; H, 6.83; N, 8.69. Found: C, 74.53; H, 6.85; N, 8.67.
ACKNOWLEDGMENTS
P. R. G., B. C. K. R., and D. A. K. thank the Council of Scientific and
Industrial Research=University Grants Commission, New Delhi, for the award of
fellowships.

CONVENIENT SYNTHESIS OF ARYL ALKYL ETHERS
2129
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