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Common Conditions:

SEAr (Electrophilic Aromatic Substitution)

Sufficiently activated aromatic rings (ex. anilines and phenols) are readily brominated at or below room temperature. The most common reagents employed are bromine and N-bromosuccinimide (NBS).[1]

Benzylic Bromination

Common conditions for benzylic bromination involve the substrate being reacted in the presence of N-bromosuccinimide (NBS) and a radical initiator (ex. AIBN or benzoyl peroxide) in carbon tetrachloride (CCl4) at elevated temperatures (ex. reflux).

Alpha Bromination

Alpha bromination generally involves enolizable ketones. Acidic conditions promote enolization. Milder brominating agents such as pyridinium hydrobromide perbromide (PHP) and phenyltrimethylammonium perbromide (PTAB) are sometimes useful alternatives.[2][3][4]


1) Smith, M. B.; March's Advanced Organic Chemistry, 7th Edition

2) Carey, F. A.; Sundberg, R. J.; Advanced Organic Chemistry, Part B: Reactions and Synthesis, 5th Edition

3) Caron, S.; Practical Synthetic Organic Chemistry

4) Burke, S. D.; Danheiser, R. L.; Handbook of Reagents for Organic Synthesis, Oxidizing and Reducing Agents