Abstract 1-Acetylazulene (1) was treated with trimethylphenylammonium tribromide in refluxing chloroform to afford 1-acetyl-3-bromoazulene (3) and 3-bromo-1-(bromoacetyl) azulene (4). In a similar manner, 3-methyl-, 3-ethyl-, 3-propyl-, and 3-methoxycarbonyl- substituted 1-acetylazulenes 2a-d gave the corresponding 3-substituted 1-(bromoacetyl) azulenes 5a-d as major products and 1-(dibromoacetyl) azulenes 6a-d as minor ones. ...