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100%
NBSac/PPh3 (2/2 mmol)
OH
Immediately
0%
OH
Br
90%
NBSac/PPh3 (2/2 mmol)
Immediately
OH
Br
10%
6
6
OH
Br
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100%
NBSac/PPh3 (1/1mmol)
30 min
OH
OH
0%
Br
5
5
OH
100%
NBSac/PPh3 (2/2 mmol)
30 min
OH
0%
OH
OH
Br
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NBSac/PPh3 (2/2 mmol)
100%
OTHP
98%
10 min
OTHP
Scheme 3.
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2.2. Benzyl iodides from benzyl alcohol using NISac/
PPh3: typical procedure
To a mixture of NISac (0.79 g, 2.5 mmol) and PPh3
(0.65 g, 2.5 mmol) in dry CH2Cl2 (25 mL) was added
benzyl alcohol (0.11 g, 1 mmol) at room temperature.
The progress of the reaction was monitored by TLC.
After completion of the reaction (Table 1, entry 1), the
solvent was evaporated. Column chromatography of
the crude mixture on silica gel using hexane/EtOAc
(1/5) gave the desired iodide in 0.19 g, 90% yield.
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Acknowledgement
We are thankful to the Shiraz University Research
Council for the partial support of this work.
ˇ
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