ChemicalBook CAS DataBase List 4-BROMO-2-METHOXY-PHENYLAMINE

4-BROMO-2-METHOXY-PHENYLAMINE synthesis

11synthesis methods

Product Name:4-BROMO-2-METHOXY-PHENYLAMINE
CAS Number:59557-91-4
Molecular formula:C7H8BrNO
Molecular Weight:202.05

90-04-0
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$5.00/5 g

59557-91-4
221 suppliers
$10.00/1g

88149-47-7 Synthesis

88149-47-7
27 suppliers
$45.00/100mg

Yield:59557-91-4 83% ，88149-47-7 9%

Reaction Conditions:

with 2,4,4,6-tetrabromocyclohexadione in dichloromethane at -10 - 20;

Steps:

4.2.7. 4-Bromo-2-methoxyaniline
o-Anisidine (470 mg, 3.60 mmol) was dissolved in dichloromethane (8 mL) and cooled to -10 °C. 2,4,4,6-Tetrabromocyclohexadione (1.56 g, 3.60 mmol) was slowly added into the above stirred solution, while the temperature was kept below -5 °C. The reaction was allowed to warm to room temperature and stirring was continued overnight. The reaction mixture was washed with sodium hydroxide (10 mL, 2 M) and then water (15 mL), dried over magnesium sulfate, filtered and evaporated to dryness. The residue was chromatographed (silica gel, dichloromethane) to afford 2,4-dibromo-6-methoxyaniline (90 mg, 9%) as a dark brown liquid. ¹H NMR (400 MHz, CDCl₃) δ 3.84 (s, 3H, OCH₃), 4.20 (br s, 2H, NH₂), 6.83 (d, J 2.1 Hz, 1H, ArH), 7.19 (d, J 2.1 Hz, 1H, ArH). The spectral data are in agreement with those reported in the literature.⁶⁵ Continued elution afforded 4-bromo-2-methoxyaniline (579 mg, 83%) as a brown solid: mp 57-59 °C (lit.⁶⁶ 56.5-58 °C; lit.⁶⁵ 60-61 °C). ¹H NMR (400 MHz, CDCl₃) δ 3.83 (s, 3H, OCH₃), 3.85 (br s, 2H, NH₂) 6.60 (d, J 7.8 Hz, 2H, ArH), 6.88-6.90 (m, 2H, ArH). The spectral data are in agreement with those reported in the literature.65 J.-M. Chrétien, F. Zammattio, E. Le Grognec, M. Paris, B. Cahingt, G. Montavon and J.-P. Quintard, J. Org. Chem. 70 (2005), pp. 2870-2873. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (25)⁶⁵