* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Recueil des Travaux Chimiques des Pays-Bas, 1925, vol. 44, p. 194
[2] Recueil des Travaux Chimiques des Pays-Bas, 1925, vol. 44, p. 194
2
[ 88149-47-7 ]
[ 16618-67-0 ]
[ 74137-36-3 ]
Reference：
[1] Recueil des Travaux Chimiques des Pays-Bas, 1925, vol. 44, p. 194
[2] Recueil des Travaux Chimiques des Pays-Bas, 1925, vol. 44, p. 194
3
[ 88149-47-7 ]
[ 74137-36-3 ]
Reference：
[1] Monatshefte fuer Chemie, 1915, vol. 36, p. 132
[2] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 2357 - 2366[3] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 12, p. 2588 - 2599
[4] Monatshefte fuer Chemie, 1915, vol. 36, p. 132
4
[ 90-04-0 ]
[ 59557-91-4 ]
[ 88149-47-7 ]
Yield
Reaction Conditions
Operation in experiment
83%
With 2,4,4,6-tetrabromocyclohexadione In dichloromethane at -10 - 20℃;
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, 9percent) 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, 83percent) 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. Chretien, 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
Reference：
[1] Tetrahedron, 2011, vol. 67, # 32, p. 5798 - 5805
[2] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2870 - 2873
5
[ 90-04-0 ]
[ 59557-91-4 ]
[ 88149-47-7 ]
Yield
Reaction Conditions
Operation in experiment
83%
With 2,4,4,6-tetrabromocyclohexadione In dichloromethane at -10 - 20℃;
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, 9percent) 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, 83percent) 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. Chretien, 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
Reference：
[1] Tetrahedron, 2011, vol. 67, # 32, p. 5798 - 5805
[2] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2870 - 2873
6
[ 90-04-0 ]
[ 88149-47-7 ]
Reference：
[1] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 2, p. 597 - 599
[2] Monatshefte fuer Chemie, 1927, vol. 48, p. 610
[3] Monatshefte fuer Chemie, 1915, vol. 36, p. 132
[4] Tetrahedron, 1993, vol. 49, # 22, p. 4809 - 4820
[5] Patent: US6660529, 2003, B2, . Location in patent: Sheet 2
[6] Russian Journal of Applied Chemistry, 2009, vol. 82, # 9, p. 1570 - 1576
7
[ 59557-91-4 ]
[ 88149-47-7 ]
Reference：
[1] Russian Journal of Applied Chemistry, 2009, vol. 82, # 9, p. 1570 - 1576
8
[ 90-04-0 ]
[ 64-19-7 ]
[ 88149-47-7 ]
Reference：
[1] Monatshefte fuer Chemie, 1915, vol. 36, p. 132
9
[ 7726-95-6 ]
[ 90-04-0 ]
[ 64-19-7 ]
[ 88149-47-7 ]
Reference：
[1] Monatshefte fuer Chemie, 1927, vol. 48, p. 610
[2] Monatshefte fuer Chemie, 1915, vol. 36, p. 132
With 2,4,4,6-tetrabromocyclohexadione; In dichloromethane; at -10 - 20℃;
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) delta 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) delta 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. Chretien, 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
At 5 C., a solution of bromine (9.8 mL, 192.5 mmol, 1.1 eq) in dichloromethane (120 mL) was added slowly to a dichloromethane solution (240 mL) of <strong>[59557-91-4]4-bromo-2-methoxyaniline</strong> (35.35 g, 175 mmol) under vigorous stirring. The reaction mixture was kept at this temperature for 2 h. After the completion monitored by TLC, the reaction mixture was poured into ice water and extracted with ethyl acetate (3*200 mL). The organic layer was combined, washed with brine (3*50 mL) and dried over sodium sulfate. Then the reaction mixture was purified by flash column chromatography (ethyl acetate/hexanes (v/v)=5/95). The product (40.3 g, yield=82%) was obtained as a red liquid. 1H NMR (600 MHz, CDCl3) delta 7.20 (d, J=1.9 Hz, 1H), 6.84 (d, J=1.8 Hz, 1H), 4.21 (s, 2H), 3.86 (s, 3H). LRMS m/z 280.0 [M+H]+.
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