[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([Br:12])[CH:3]=1.[CH:13](OCC)(OCC)OCC.[N-:23]=[N+:24]=[N-:25].[Na+]>CC(O)=O>[Br:12][C:4]1[CH:3]=[C:2]([N:1]2[CH:13]=[N:25][N:24]=[N:23]2)[CH:7]=[CH:6][C:5]=1[CH2:8][C:9]([OH:11])=[O:10]A solution of (4-amino-2-bromophenyl)acetic acid (230 mg, 1 mmol) and triethyl orthoformate (444 mg, 3 mmol) in 8 mL of HOAc was added sodium azide (80 mg, 1.2 mmol), and the mixture was heated to 100° C. for 3 hours. The reaction mixture was cooled to ambient temperature and the solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by prep-TLC to afford [2-bromo-4-(1H-tetrazol-1-yl)phenyl]acetic acid. 1H-NMR (300 MHz, MeOD) δ ppm 9.78 (s, 1H), 8.16 (s, 1H), 7.83˜7.87 (m, 1H), 7.60˜7.63 (m, 1H), 3.89 (s, 2H).
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