[CH2:1]([O:3][C:4]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C1C(=O)N([Br:23])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>FC(C1C=CC=CC=1C)(F)F>[Br:23][CH2:15][C:13]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([O:3][CH2:1][CH3:2])[CH:14]=1To a solution of ethyl 2-ethoxy-4-methylbenzoate (100 mg, 0.481 mmol) in 2 mL of trifluoromethyl toluene was added NBS (94 mg, 0.529 mmol) and AIBN (10 mg) in portions. The mixture was heated to reflux and stirred for 24 h. The reaction mixture was concentrated, diluted with 10 mL of EA, washed with 5 mL of 4 N NaOH, 5 mL of brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford ethyl 4-(bromomethyl)-2-ethoxybenzoate as brown oil (42 mg, 30%), which was used for the next step directly.
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