Table 2.
Bromination of phenol (13) under solvent-free PV-PTFE conditions.
| Entry | Conditions | Product (% yield)a | Time (min) |
| 1 | Br2 (1.1 equiv) | 4-bromophenol (14) (89) | 10 |
| 2 | Br2 (excess) | 14 (86) | 10 |
| 3 | Br2 (2.2 equiv) | 2,4-dibromophenol (15) (82) | 30 |
| 4 | Br2 (excess), closed system | 15 (90) | 30 |
| 5 | Br2 (excess), open to air | (15) (41) + 2,4,6-tribromophenol (16) (46) | 240 |
| 6 | Br2 (excess), H2O | 16 (91) | 60 |
aIsolated yields.