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ChemicalBook CAS DataBase List 2-Amino-4-bromophenol
40925-68-6

2-Amino-4-bromophenol synthesis

11synthesis methods
-

Yield:40925-68-6 99%

Reaction Conditions:

with Rh/C;hydrogen in tetrahydrofuran at 20; for 11 h;

Steps:

43 5.1.43 2-Amino-4-bromophenol (63)

To a solution of 4-bromo-2-nitrophenol (50.7 g, 233 mmol) in THF (500 mL) was added 5% Rh/C (5.00 g), and stirred at room temperature for 11 h under hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated to give 63 (43.3 g, 99%) as a brown solid: mp 133-135 °C; 1H NMR (400 MHz, DMSO-d6) δ 9.29 (1H, s), 6.72 (1H, d, J = 2.4 Hz), 6.56 (1H, d, J = 8.3 Hz), 6.50 (1H, dd, J = 8.3, 2.4 Hz), 4.91 (2H, br s); IR (ATR) 3062, 1497, 1444, 1437, 1279 cm-1; HRMS (ESI) m/z calcd for C6H7BrNO [M+H]+ 187.9706; found 187.9704.

References:

Fukaya, Takayuki;Kodo, Toru;Ishiyama, Takeo;Kakuyama, Hiroyoshi;Nishikawa, Hiroyuki;Baba, Satoko;Masumoto, Shuji [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 18,p. 5568 - 5582]

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