Chloroform → 4-Bromo-2,5-ditert-butylaniline

반응식

[Br:1]Br.[C:3]([C:7]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][C:8]=1[NH2:9])([CH3:6])([CH3:5])[CH3:4].C(Cl)(Cl)Cl.[OH-].[Na+]>CO>[Br:1][C:12]1[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][C:8]([NH2:9])=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[CH:13]=1

참가 물질

실험 절차

Bromine (271 μL, 5.29 mmol) was added dropwise via syringe to a solution of 2,5-di-tert-butylaniline (1.09 g, 5.29 mmol) in methanol (80 mL). The solution was stirred at room temperature for 10 min. Chloroform and 0.1 N NaOH were added and the organic layer was dried (Na2SO4), filtered and concentrated to a pale yellow solid (1.46 g, 97%): mp 89-90° C.; 1H NMR δ1.38 (s, 9H), 1.45 (s, 9H), 3.77 (brs, 2H), 6.68 (s, 1H), 7.35 (s, 1H); 13C NMR δ29.4, 29.7, 33.7, 35.8, 111.0, 117.4, 133.1, 133.8, 143.3, 145.9; FAB-MS obsd 283.0936; calcd 283.0937; Anal calcd for C14H22BrN: C, 59.16; H, 7.80; Br, 28.11; Found, C, 59.33; H, 7.78; Br, 27.86.