M.A. Carroll et al. / Journal of Fluorine Chemistry 128 (2007) 127–132
131
solvent was removed in vacuo to give the crude product.
Crystallisation gave 5 as a white crystalline solid (2.17 g,
4.63 mmol, 93%); mp 144–146 8C (from dichloromethane–
hexane); Anal. Calcd. for C17H16IO4F3: C, 43.6; H, 3.4. Found
C, 43.6; H, 3.5. IR (KBr): n 3082, 2839, 1656, 1564, 1440,
1286, 1174; dH (270 MHz; d6-Me2SO) 8.28 (1H, d, H60 J 8 Hz),
8.17 (1H, d, H6 J 9 Hz), 7.62 (1H, t, H40 J 8 Hz), 7.27 (1H, d,
H30 J 8 Hz), 7.07 (2H, m, H3/H50), 6.83 (1H, dd, H5 J 3, 9 Hz),
3.93 (3H, s, 20-OMe), 3.77 (3H, s, 4-OMe), 2.60 (3H, s, 2-CH3);
dC (68 MHz; d6-Me2SO) 162.7, 156.8, 143.4, 139.4 (C6), 137.6
(C60), 135.0 (C40), 123.8 (C50), 117.2 (C3), 115.2 (C5), 113.4
(C30), 110.7, 107.4, 57.4 (20-OMe), 56.1 (4-OMe), 25.4 (Me);
m/z (FAB) 356(M + H+, 16%), 355(M+, 100). [Found: M+,
355.0192. C15H16IO2 requires 355.0195].
0.05 mmol) in DMF (2.5 mL) were added to a carousel tube
[43] (predried at 140 8C, evacuated and flushed with nitrogen).
The carousel tube was then placed on a carousel reactor
preheated to 90 8C and heated for the required time. At the time
intervals stated in Table 5 aliquots (0.3 mL) were taken, cooled
to room temperature rapidly, diluted with DMF (0.4 mL) and
analysed by 19F NMR. The yield was calculated using 3-
trifluoromethylanisole as an internal standard.
Acknowledgement
We thank GE-Healthcare for funding and the EPSRC for
provision of the Swansea Mass Spectrometry Service.
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´
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