Synthesis of chloropolyfluoroarenes from polyfluoroarenethiols and PCl5

Article abstract of DOI:10.1134/S1070428016020068

Replacement of the thiol group in polyfluoroarenethiols with chlorine was performed by treating with PCl₅ as chlorinating agent. By heating in ampules at 200-220°C polyfluoro- and polyfluorochloroarenethiols with PCl₅ mono- and dichloropolyfluoroarenes and also 1,2,4-trifluorotrichlorobenzene were synthesized. Dichloropolyfluoroarenes contain chlorine atoms in ortho- and para-positions.

Full text of DOI:10.1134/S1070428016020068

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2016, Vol. 52, No. 2, pp. 200–205. © Pleiades Publishing, Ltd., 2016.
Original Russian Text © P.V. Nikul’shin, А.M. Maksimov, V.Е. Platonov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 2,
pp. 217–221.
Synthesis of Chloropolyfluoroarenes
from Polyfluoroarenethiols and PCl5
P. V. Nikul’shin, А. M. Maksimov, and V. Е. Platonov
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences,
pr. Academika Lavrent’eva 9, Novosibirsk, 630090 Russia
e-mail: platonov@nioch.nsc.ru
Received October 28, 2015
Abstract—Replacement of the thiol group in polyfluoroarenethiols with chlorine was performed by
treating with PCl5 as chlorinating agent. By heating in ampules at 200–220°C polyfluoro- and
polyfluorochloroarenethiols with PCl5 mono- and dichloropolyfluoroarenes and also 1,2,4-
trifluorotrichlorobenzene were synthesized. Dichloropolyfluoroarenes contain chlorine atoms in
ortho- and para-positions.
DOI: 10.1134/S1070428016020068
It is known that thiol group in aliphatic thiols can
be substituted by chlorine atom in mild conditions
under the action of chlorinating agents and
triphenylphosphine. For instance, in reactions of these
thiols with CCl4 and triphenylphosphine the
corresponding chloroalkanes are obtained [1, 2]. The
configuration inversion is observed in the process [1].
In patent [2] the ionic mechanism of such
transformation was suggested. At the same time the
substitution of the thiol group with chlorine in
butanethiol under the treatment with CCl4, triethyl
phosphite, and benzoyl peroxide was described. The
process evidently involved radical intermediates [3].
The thiol group in aliphatic thiols may also be
substituted by chlorine atom in mild conditions
under treatment with sulfuryl chloride and
triphenylphosphine [6]. First the aliphatic thiols are
processed with sulfuryl chloride then follow the
reaction of intermediately generated sulfenyl chloride
with triphenylphosphine affording the chloro-
derivative. A similar process occurred with dialkyl
disulfide. In the aromatic series for this system only
the transformation is described of benzenethiol,
diphenyl disulfide, and para-thiocrezole into chlo-
robenzene and para-chlorotoluene in low yields [6].
Still et al. mentioned in this publication a very limited
possibility of such type transformations in aromatic
compounds compared to aliphatic series and in this
connection did not suggest any considerations on the
reaction mechanism in the aromatic compounds.
Aliphatic thiols were converted in chloroalkanes in
reactions with chlorocarbonylsulfenyl chloride and tri-
phenylphosphine. Therewith the reaction between thiols
and chlorocarbonylsulfenyl chloride first provided in
high yields alkyl chlorocarbonyl disulfides and then
these compounds reacted with triphenylphosphine with
the formation of chloroalkanes [4].
Recently we developed a convenient method of
introducing chlorine atoms into polyfluoroarenes by
thermal replacement of a thiol group for a chlorine
atom. The thiol function is easily and selectively
introduced into polyfluoroarenes by reactions of
nucleophilic substitution [7, 8]. By this method a series
of chloropolyfluoroaromatic compounds was synthe-
sized in high yields [7, 8]. This reaction proceeds at
high temperatures (~400°C) in a flow system.
A method providing haloalkanes in high yields was
developed applying the reaction of thiols with N-
chlorosuccinimide and triphenylphosphine. The pro-
cess was believed to occur with the participation of an
intermediately generated quaternary phosphonium salt
containing an alkyl sulfide group. This salt via SN2
reaction with the chloride anion gives the chloroalkane
[5].
In the present study the selective substitution of
thiol group in polyfluoro- and polyfluorochloroare-
200

SYNTHESIS OF CHLOROPOLYFLUOROARENES FROM POLYFLUOROARENETHIOLS
201
Cl
SH
nethiols by the chlorine atom using PCl5 as chlorine-
ting reagent is described. This process occurs at ~200°C.
2PCl5
F
F
By heating of pentafluorobenzenethiol 1 with ~1 mole
of PCl5 in an ampule at ~200°C during 5 h the
substitution of the thiol group for the chlorine atom
occurs while the reaction mixture contains along with
200_220°C, 5 h
X
X
5, 7, 9
6, 8, 10
chloropentafluorobenzene
2
bis(pentafluorophenyl)
X = H (5, 6), Cl (7, 8), CF3 (9, 10).
disulfide 3 and pentafluorobenzenesulfenyl chloride 4
(ratio of 2–3–4 ~83 : 9 : 8, according to 19F NMR
data). By increasing the time of the reaction to 16 h the
fraction in the reaction mixture of compound 2 grows
and the fractions of compounds 3 and 4 decrease (ratio
of 2–3–4 ~91 : 5 : 4, according to 19F NMR data).
After heating for 24 h we managed to obtain almost
individual arene 2 in 89% yield. This may prove that
~1 mole of PCl5 is sufficient for the use in the reaction,
however it requires longer heating compared to
reaction of compound 1 with 2 moles of PCl5. In this
case the reaction takes 5 h and leads to practically
individual compound 2 in a high yield.
bromotetrafluorobenzenethiol 11 at 180°C resulted as
well in considerable substitution of bromine by the
chlorine atom. By increasing the reaction temperature
to ~240°C practically individual compound 8 was
obtained.
Cl
Cl
SH
2PCl5
F
F
+
F
Cl
Br
Br
11
8
12
2PCl5
Cl
SH
F
5 h, 93%
~62%
~99%
36%
<1%
~180°C, 5 h
~240°C, 5 h
200°C
F
From nonafluoroindane- and 6-chlorooctafluoroin-
dane-5-thiols 13 and 14 we obtained 5-chloronona-
fluoro- and 5,6-dichlorooctafluorindanes 15 and 16.
1.2PCl5
1
2
24 h, 89%
By heating compounds 3 and 4 with PCl5
chloroarene 2 was also obtained.
SH
Cl
2PCl5
F
F
F
F
~220°C, 5 h
X
X
Cl
SX
13, 14
15, 16
2PCl5
X = F (13, 15), Cl (14, 16).
F
F
~200°C, 5 h
3, 4
2
By heating in ampule the mixture of 2,4-, 3,4-, and
2,5-dichlorotrifluorobenzenethiols in the ratio 70 : 18 :
12 (19F NMR) with PCl5 we obtained practically
individual 1,2,4-trichlorotrifluorobenzene 17 in 90%
yield (Scheme 1).
X = SC6F5 (3), Cl (4).
In similar way reactions of para-substituted thiol 1
derivatives proceed. Hence, by heating 2,3,5,6-
tetrafluorobenzenethiol 5 with PCl5 we obtained 1-
chloro-2,3,5,6-tetrafluorobenzene 6, and from 4-chlo-
rotetrafluorobenzenethiol 7, 1,4-dichlorotetrafluoro-
benzene 8. 4-Trifluoromethyl-2,3,5,6-tetrafluoroben-
zenethiol 9 in reaction with PCl5 gives a high yield of
4-chloroheptafluorotoluene 10.
Scheme 1.
SH
F
Cl
Cl
F
SH
F
SH
Cl
Cl
2.2PCl5
F
+
+
~200°C,
5 h
Cl
At the same time the attempt to obtain 1-bromo-4-
chlorotetrafluorobenzene 12 by chlorinating 4-
Cl
Cl
Cl
Cl
17
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 52 No. 2 2016

NIKUL’SHIN et al.
202
To understand the process of substitution of the
(1)
(2)
PCl3 + Cl2
2Cl
PCl5
Cl2
PCl5
thiol group for chlorine atom in reactions of
polyfluoroarenethiols with PCl5 we studied the
behavior of compound 1 in reactions with PCl5 at
various temperatures.
Δ
C6F5SSC6F5
2C6F5SCl
PCl3
+
+
(3)
(4)
3
4
At 20ºC thiol 1 and PCl5 afforded only disulfide 3,
in keeping with the data of thiols transformations into
disulfides in reactions with PCl5 [9]. By heating thiol 1
with PCl5 in an ampule at 100°C a mixture formed of
sulfenyl chloride 4 and compound 3, while arene 2 was
not obtained according to 19F NMR data, (Scheme 2).
C6F5S
C6F5SCl
+ Cl
4
A
Cl
SCl
F
F
F
F
C F SCl
+
Cl
SCl C F Cl
6
5
+
6
5
4
2
F
(5)
Scheme 2.
B
PCl3
S
S
SH
SCl
2PCl5
C6F5SCl
F
F
F
F
+
+ S PCl3
Cl
Cl
S
PCl3
18
C
3
4
1
~20°C
~100°C, 5 h
:
:
0
~100
~69
thiol group in polyfluoroarenethiols by chlorine atom
at higher temperatures (180–220°С) could proceed by
the homolytic mechanism. Here the source of chlorine
is PCl5 (eq. 1). Cl2 may also dissociate to chlorine atoms
(eq. 2) [11, 12, 15]. Sulfenyl chloride 4 formed at heating
disulfide 3 with PCl5 (eq. 3) may decompose to chlorine
atom and thiyl radical А (eq. 4). The formation of
compound 2 from sulfenyl chloride 4 goes, probably,
through the radical σ-complex B (eq. 5) [7]. Radical
SCl eliminated at the decomposition of σ-complex B
could generate the phosphoranyl radical C by
interaction with PCl3. The latter at β-decomposition
results in thiophosphoryl chloride 18 that we have
registered by 31P NMR spectrum and GC-MS. It is
known that phosphoranyl radicals, despite their
relative stability, may undergo β-decomposition,
including the one with generation of S=P bond [16].
31
From disulfide 3 and PCl5 at 100ºC a mixture was
obtained of initial compound 3 and pentafluorophenyl-
sulfenyl chloride 4 in a ratio 68 : 32 (according to 19F
NMR data).
The generation of disulfide 3 from thiol 1 and PCl5
at 20°C may occur through the transformations shown
in Scheme 3. Considering that in crystalline state PCl5
has ionic structure [PCl4]+[PCl6]– [10], the generation
of sulfenyl chloride 4 may occur involving cation
[PCl4]+. Compound 4 while interacting with thiol 1
transforms in disulfide 3, as has been proved by a special
experiment. The formation of disulfide 3 from thiol 1
and PCl5 without participation of sulfenyl chloride 4,
evidently, is also possible. The interaction of disulfide
3 with Cl2 may cause the formation of sulfenyl chlo-
ride 4 in the reaction of thiol 1 with PCl5 at ~100°C.
The participation of Cl2 in this process may be due to
the decomposition of PCl5 at heating [11–13].
Radical А also could have formed sulfenyl chloride
4 and radical PCl4 (eq. 6) by abstracting chlorine from
PCl5. Interactions of this type were described in [11,
12]. Phosphoranyl radical PCl4 decomposes into PCl3
and Cl [11] (eq. 7).
Scheme 3.
C6F5SH
_HCl
PCl5
C6F5S
C6F5SCl
(6)
PCl5
PCl4
+
+
C6F5SH
[C6F5SCl]
C6F5SSC6F5
~20°C, _HCl,
_PCl3
A
4
1
4
3
PCl4
PCl3
Cl
(7)
+
Previously it was assumed that in reactions of PCl5
with olefins the transfer from heterolytic to homolytic
mechanism was possible as the temperature of reaction
was raised [14]. In this connection the substitution of
A similar system may be suggested to describe the
transformations of other polyfluoroarenethiols into
chloropolyfluoroarenes.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 52 No. 2 2016

SYNTHESIS OF CHLOROPOLYFLUOROARENES FROM POLYFLUOROARENETHIOLS
203
EXPERIMENTAL
of compound 2 (content in the mixture according to
GC data ~100%).
Analytic and spectral measurements were carried
out in Chemical Service Center of joint usage of the
Siberian Branch of the Russian Academy of Sciences.
From 3.12 g (15.59 mmol) of compound 1 and
3.76 g (18.06 mmol) of PCl5 (200–202°C, 24 h) were
obtained 2.82 g (89%) of compound 2, content in the
mixture ~100% (GC).
NMR spectra were recorded on a Bruker AV-300
[282.4 (19F) and 300 (1H) МHz] spectrometer in CCl4
with added (CD3)2СO, internal reference С6F6 and
HMDS (0.04 ppm from TMS). 31P NMR spectra were
recorded on a Bruker AV-400 (162.0 МHz) spectro-
meter, external reference H3PO4. Positive values of
chemical shifts correspond to the signal downfield
shift. For GC-MS a chromatograph HP 5890 with
mass-selective detector HP 5971 was used and a
chromatograph Agilent 6890N with the system Agilent
5973N. Energy of ionizing electrons was 70 eV. The
separation of substances was performed using column
HP-5 30 m × 0.25 mm × 0.25 µm, carrier gas helium,
flow rate 1 mL/min, column temperature 50–280°С,
ion source temperature 173°С. GC analysis was
carried out on a chromatograph HP 5890 with a
column HP-5, 30 m × 0.52 mm × 2.6 µm and a
detector of thermal conductivity.
Similarly from 3.21 g (8.06 mmol) of compound 3
and 3.58 g (17.91 mmol) of PCl5 (203–205°C, 5 h)
were obtained 2.94 g (88%) of compound 2, content in
the mixture 97.2% (GC).
From 3.50 g (14.92 mmol) of compound 4 and
6.40 g (30.73 mmol) of PCl5 (203–205°C, 5 h) were
obtained 2.62 g (85%) of compound 2, purity 98.4%
(GC).
1-Chloro-2,3,5,6-tetrafluorobenzene (6). From
3.33 g (18.28 mmol) of compound 5 and 7.93 g
(38.08 mmol) of PCl5 (198–200°C, 5 h) were obtained
3.10 g (92%) of compound 6, purity 99.7% (GC).
1,4-Dichlorotetrafluorobenzene (8). By heating
3.29 g (15.19 mmol) of thiol 7 and 6.60 g
(31.69 mmol) of PCl5 (201–203°C, 5 h) were obtained
3.01 g (90%) of compound 8, purity 99.5% (GC).
Initial polyfluoroarenethiols were obtained by the
method [17]. Isomeric mixture of dichlorotrifluoroben-
zenethiols was prepared from technical mixture of о-,
m-, p-C6F4Cl2 and KSH (yield 90%) [18].
4-Chloroheptafluorotoluene (10). From 3.10 g
(12.39 mmol) of compound 9 and 5.22 g (25.07 mmol)
of PCl5 (219–221°C, 5 h) were obtained 2.89 g (92%)
of compound 10, purity ~100% (GC).
The formation of compounds 3 and 4 and final
products of polyfluoroarenethiols chlorination was
proved by comparing their 19F NMR spectra with
published data [7, 8, 18].
Reactions of 4-bromotetrafluorobenzenethiol
(11) with PCl5. а. From 3.25 g (12.45 mmol) of thiol
11 and 5.35 g (25.69 mmol) of PCl5 (179–181°C, 5 h)
were obtained 2.64 g of a mixture containing compounds
8 62.4% and 12 36%, according to GC data.
Chlorination of polyfluoroarenes. Method 1.
Polyfluoroarenethiol was charged in an ampule and
PCl5 was added by portions. After the gas evolution
finished the ampule was sealed, placed into a metal
case, and heated. After the reaction completed the
ampule was cooled, opened, its content was placed into
a flask under a layer of water with ice (80–100 g),
stirred for 2 h by magnetic stirrer to hydrolyze the
phosphorus compounds, then alkalinized with Na2CO3,
stirred for 2 h more, and subjected to steam distillation.
The reaction product was separated, dried with CaCl2,
and analyzed by GC and 19F NMR methods.
Compounds 2, 6, 8, 10, 12, 15, 16, and 17 were
obtained.
b. At 238–240°C (5 h) from 3.48 g (13.33 mmol) of
compound 11 and 5.48 g (26.32 mmol) of PCl5 were
obtained 2.62 g of a mixture containing compounds 8
99.1% and 12 0.6%, according to GC data.
1-Bromo-4-chlorotetrafluorobenzene (12). 19F
NMR spectrum (from the spectrum of a mixture of
compounds 8 and 12), δ, ppm: 22.6 m (F3,5), 30.3 m
(F2,6). Found M+ 262 1Cl, 1Br. Calculated M 261.88.
5-Chlorononafluoroindane (15). From 3.48 g
(11.15 mmol) of compound 13 and 4.76 g (22.86 mmol)
of PCl5 (218–220°C, 5 h) were obtained 3.19 g (90%)
of compound 15, purity 99% (GC).
Chloropentafluorobenzene (2). From 3.16 g
(15.79 mmol) of compound 1 and 6.69 g (32.13 mmol)
of PCl5 (201–203°C, 5 h) were obtained 2.96 g (93%)
5,6-Dichlorooctafluoroindane (16). Similarly by
heating (218–220°C, 5 h) 3.04 g (9.25 mmol) of
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 52 No. 2 2016

NIKUL’SHIN et al.
204
compound 14 with 3.83 g (18.39 mmol) of PCl5 were
obtained 2.83 g (92%) of a substance containing
compound 16 99.1%, according to GC data.
This method was applied to perform the reactions
of compounds 1, 3, and 4 with PCl5 in various
conditions:
1,2,4-Trichlorotrifluorobenzene (17) [18]. By chlo-
rination of 3.26 g (13.99 mmol) of a mixture of 2,4-,
3,4- and 2,5-dichlorotrifluorobenzenethiols (~70 : 18 : 12
according to 19F NMR data) and 6.51 g (31.26 mmol)
of PCl5 at 198–200°C (5 h) were obtained 2.97 g
(90%) of a substance containing compound 17 99.9%,
according to GC data.
а. After mixing from 0.0905 g (0.45 mmol) of
compound 1 and 0.1898 g (0.91 mmol) of PCl5 at room
temperature we obtained pure compound 3 (19F NMR
data).
b. From 0.1760 g (0.88 mmol) of compound 1 and
0.3677 g (1.77 mmol) of PCl5 by heating at 100°C
during 5 h a mixture was obtained of compounds 3 and
4 in a ratio ~69 : 31 (19F NMR data).
Compounds (2 and 18). а. In an ampule was
charged 1.76 g (8.79 mmol) of thiol 1 and then by
portions 2.13 g (10.22 mmol) of PCl5 was added. After
the end of gas evolution the ampule was sealed, placed
into a metal case, and held for 18 h at 200°C. Then the
ampule was cooled and opened. We obtained 3.40 g of
a mixture of compound 2 (49%) and PSCl3 18 (45%)
according to GC-МS data.
c. By increasing the temperature to 198–200°C
(5 h) from 0.2552 g (1.28 mmol) of compound 1 and
0.2638 g (1.27 mmol) of PCl5 a mixture was obtained
of compounds 2, 3, and 4 in a ratio ~83 : 9 : 8 (19F
NMR data).
d. Similarly from 0.1341 g (0.67 mmol) of
compound 1 and 0.1570 g (0.75 mmol) of PCl5 (199–
201°C, 16 h) a mixture was obtained containing
compounds 2, 3, and 4 in a ratio ~91 : 5 : 4 (19F NMR
data).
b. In an ampule was charged 3.15 g (15.74 mmol)
of thiol 1 and then by portions 6.53 g (31.36 mmol) of
PCl5 was added. After the end of gas evolution the
ampule was sealed, placed in a metallic case, and held
for 5 h at 201–203°C. Then the ampule was cooled,
opened, its content was placed into flask with ice
(~70 g). To the mixture 10.51 g of Na2CO3 was added,
the reaction products were subjected to steam
distillation, separated, dried with CaCl2. We obtained
3.60 g of a mixture containing according to GC-МS
data 80.7% of compound 2 and 16.6% of PSCl3 18.
From 0.18 g (0.45 mmol) of compound 3 and
0.19 g (0.48 mmol) of PCl5 at 100°C during 5 h a
mixture was obtained of compounds 3 and 4 in a ratio
~68 : 32 (19F NMR data).
Thermolys of compound (4). From 0.22 g
(0.94 mmol) of compound 4 at 200°C during 24 h a
mixture was obtained of compound 2 and decafluoro-
diphenyl polysulfides in a ratio ~83 : 17 (19F NMR
data).
The identification of compound 18 was performed
using the 31P NMR data [19], and also by comparing
the complete mass-spectrum, obtained by electronic
ionization, with a spectrum from the library W8N08
Thermolys of compound (4) in the presence of
PCl3. From 0.25 g (1.08 mmol) of compound 4 and
0.15 g (1.09 mmol) of PCl3 at 200°C during 24 h a
mixture was obtained of compounds 2, 3, and bis-
(pentafluorophenyl) sulfide in a ratio ~83 : 15 : 2 (19F
NMR data). Formation of PSCl3 was confirmed by the
31P NMR data.
[20], where
a
concise mass-spectrum of
thiophosphoryl chloride was published. Complete
mass spectrum of compound 18 synthesized by the
method [21], m/z (Irel, %): 174 (2.8), 172 (20.6), 170
(59.0), 168 (58.0) [Cl3PS], 138 (1.5), 136 (2.0) [Cl3P],
137 (13.8), 135 (70.6), 133 (100.0) [Cl2PS], 105 (1.4),
103 (8.2), 101 (12.4) [Cl2P], 100 (2.5), 98 (6.0) [ClPS],
68 (1.8), 66 (5.0) [ClP], 63 (9.0) [PS], 37 (0.7), 35
(1.9) [Cl].
Reaction of thiol (1) with sulfenyl chloride (4).
To 0.1416 g (0.60 mmol) of sulfenyl chloride 4 at room
temperature was added dropwise 0.1167 g (0.58 mmol)
of thiol 1. After the gas evolution stopped the obtained
mixture was dissolved in ~2 mL of CH2Cl2 and
analyzed with 19F NMR. The reaction mixture
contained compounds 3 and 4 in a ratio ~ 93 : 7 (19F
NMR data).
Metod 2. In an ampule was charged compound 1,
3, and 4 and by portions PCl5 was added. After the end
of gas evolution the ampule was sealed, placed in a
metal case, and heated. Then the ampule was cooled,
opened, its content was dissolved in 2 mL of
methylene chloride, and analyzed with 19F NMR.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 52 No. 2 2016

SYNTHESIS OF CHLOROPOLYFLUOROARENES FROM POLYFLUOROARENETHIOLS
205
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