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Optimization of batch conditions for the mono ortho-bromination reaction.
| Entry | NBS (mol %) | pTsOH (mol %) | Ratio (Relative % at 285 nm) | Isolated Yield 10 (%) |
||
|---|---|---|---|---|---|---|
| 9 | 10 | 11 | ||||
| 1 a,b | 100 | 10 | 6 | 87 | 7 | -- |
| 2 b | 100 | 10 | 5 | 93 | 2 | -- |
| 3 | 100 | 10 | 3 | 94 | 3 | 92% |
| 4 | 110 | 10 | 0 | 88 | 12 | 86% |
| 5 | 100 | 0 | 15 | 77 | 8 | 74% |
| 6 | 100 | 20 | 3 | 93 | 4 | 90% |
a NBS added as a single portion at the start of the reaction and then reaction stirred for 25 min; b Reaction conducted in dry methanol.
