TABLE 2.
One-Pot Bromination of p-Tolylethyne with Hypervalent iodine Reagent.
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Entry | PIDA-1 (equiv) | NaBr-1 (equiv) | PIAD-2 (equiv) | NaBr-2 (equiv) | t2 (h) | % Yield (2a:3a:4a:5a:6a) a |
1 | 2.0 | 4.0 | — | — | 0 | 54 (0:30.2:15.9:0:53.9) |
2 | 3.0 | 6.0 | — | — | 0 | 74 (3.8:5.9:3.5:0:86.8) |
3 | 2.0 | 4.0 | 2.0 | 4.0 | 3 | 80 (0:0:0:9.2:90.8) |
4 | 4.0 | 6.0 | 1.0 | 3.0 | 3 | 93 (0:0:0:6.7:93.3) |
The yield and the molar ratio of 2a to 3a to 4a to 5a to 6a were determined via 1H NMR, spectroscopy using acetophenone as the internal standard.