A Br₂ CH3OH 1.03 2. DMS KMnO4, NaOH cold HI mCPBA 1. OSO4 2. H₂O2 1.03 2. (CH3)2S 17 18 16 15 B 19 CH3CO3H (peroxyacid) 14 13 H₂ Pd or Pt (catalyst) HBr 20 1 1. МСРВА 2. H3O* 12 11 10 Pd or Ni (catalyst) 2 Br OCH 3 Looks for "Br OCH3 D2 (deuterium) 3 4 5 6 7 8 EtOH Br₂ C BH 3 THF Br HBr ROOR (peroxide) H₂O H₂SO4 ""OCH 3 HCI 1. BH 3 THF 2. H₂O2, NaOH Br₂ Br₂ H₂O D OCH3 Br + Br OCH3 OCH3 Br œ œ œ œ 'Br Br 'OCH 3 OCH 3
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