[Br:1][C:2]1[CH:16]=[C:15]([CH:17]=O)[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C([BH3-])#[N:20].[Na+].O>CO.CC(O)=O>[NH2:20][CH2:17][C:15]1[CH:14]=[CH:13][C:3]([O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:2]([Br:1])[CH:16]=1t-Butyl 2-(2-bromo-4-formylphenoxy)acetate (1) (0.5 g, 1.59 mmol, 1 eq) was dissolved in MeOH (23 mL) along with HOAc (14 mL) and NH4OAc (6.23 g, 81 mmol; 51 eq). After stirring at room temperature room temperature for 4 h, sodium cyanoborohydride (146 mg; 2.27 mmol, 1.4 eq) was added and the mixture was stirred for an additional 18 h at room temperature. Water (4 mL) was added and the mixture was concentrated in vacuo. The resultant residue was purified by preparative HPLC to afford 91 mg (18.2%) of t-butyl 2-(4-(aminomethyl)-2-bromophenoxy)acetate (6).
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