To
a
solution
of
3-aminobenzenethiol
(4.43
g,
35.4
mmol)
in
THF
(225
mL)
was
added
sodium
hydride
(1.77
g,
44.3
mmol)
at
0
°C
and
stirred
for
30
min.
Then,
2,2,2-trifluoroethyl
4-
methylbenzenesulfonate
(9.0
g,
35.4
mmol)
was
added
and
the
reaction
mixture
was
stirred
for
18
h.
The
reaction
mixture
was
quenched
with
water
(20
mL)
and
extracted
with
EtOAc
(2x50
mL).
The
combined
organic
extracts
were
washed
with
water,
dried
over
Na2SO4,
fdtered,
and
concentrated
under
reduced
pressure.
The
crude
residue
was
purified
by
flash
chromatography
through
a
Redi-Sep
pre-packed
silica
gel
column,
eluting
with
a
gradient
of
5
%
to
10
%
EtOAc
in
hexanes,
to
give
3-((2,2,2-
trifluoroethyl)thio)aniline
(5
g,
68
%
yield)
as
a
pale
brown
oil.
