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33644643454
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note
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All products have been identified by GC/MS.
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35
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33644660333
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note
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2 solution that afforded 3-chloro-1,2-dibromo-3- chlorobenzene (4a) in 94% assay yield.
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-
-
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36
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33644650150
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note
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At the same time only small amounts of side products (1a and 6) according to Scheme 1 were observed.
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37
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33644653522
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note
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13C NMR data confirmed that within 20 min the deprotonation reaction primarily formed the lithiated product 2b.
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-
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38
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0000844123
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and references therein
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For examples of lithium-zinc transmetalation and Negishi-type cross-coupling reactions, see: (a) Karig, G.; Spencer, J. A.; Gallagher, T. Org. Lett. 2001, 3, 835 and references therein.
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33644653832
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note
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(b) Examples for the cross-coupling reaction of (2-bromophenyl)(iodo)zinc were described in ref 24.
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40
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33644651079
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note
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1,3-Bromofluorobenzene (1b) was chosen for the NMR experiment, because the formation of 2-bromo-6-fluorophenyllithium (2b) appeared as a homogeneous reaction mixture under the standard reaction conditions.
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41
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33644658729
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13C NMR chemical shifts of aryllithium and arylzine was reported: Gauthier, D. R., Jr.; Szumigala, R. H.; Dormer, P. G.; Armstrong, J. D., III; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 375.
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0003975691
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51
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33644642160
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note
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The same regioselectivity in the deprotonation step with LiTMP has been observed: ref 12(b).
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-
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52
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33644650807
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note
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The lithiated methyl-3-bromobenzoate (2g) underwent self-conden sation as the major side product after bromination was initiated.
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