Uses
1-(4-(Benzyloxy)-3-nitrophenyl)-2-bromoethanone, can be used as an intermediate in the synthesis of Arformoterol Tartrate (A767505), which is a derivative of Arformoterol, a long acting beta-adrenoceptor agonist drug indicated for the treatment of chronic obstructive pulmonary disease (COPD).
Synthesis
Step 2: 200 g of 4-benzyloxy-3-nitroacetophenone (Intermediate 1) was dissolved in 1000 mL of dichloromethane and 277 g of trimethylphenylammonium tribromide was added. The reaction mixture was heated to 300 °C and kept for 4 hours. After completion of the reaction, the residual liquid was poured into water, filtered, washed and dried to give 253 g of 3'-nitro-4'-benzyloxy-2-bromoacetophenone in 98% yield.
References
[1] Patent: CN108358791, 2018, A. Location in patent: Paragraph 0016; 0020
[2] Canadian Journal of Chemistry, 2011, vol. 89, # 3, p. 364 - 384
[3] Chirality, 2010, vol. 22, # 2, p. 206 - 211
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 249 - 253
[5] Tetrahedron Asymmetry, 2000, vol. 11, # 13, p. 2705 - 2717
