ChemicalBook CAS DataBase List 2-AMINO-5-BROMOPHENOL

2-AMINO-5-BROMOPHENOL synthesis

9synthesis methods

Product Name:2-AMINO-5-BROMOPHENOL
CAS Number:38191-34-3
Molecular formula:C6H6BrNO
Molecular Weight:188.02

27684-84-0

38191-34-3

General procedure for the synthesis of 2-amino-5-bromophenol from 5-bromo-2-nitrophenol: 5-bromo-2-nitrophenol (0.292 g, 1.34 mmol) was dissolved in 0.5% aqueous sodium hydroxide solution (30 mL) and stirred until completely dissolved. Sodium bisulfite (2.00 g, 85% pure, 9.76 mmol) was added to the reaction system and the reaction was stirred at room temperature for 15 minutes. After completion of the reaction, the reaction mixture was slowly acidified with dilute hydrochloric acid to pH 5. Subsequently, the reaction mixture was extracted with diethyl ether (40 mL) in three portions, the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to give the crude product 2-amino-5-bromophenol (0.533 g, melting point 99.5-100.5 °C). The crude product was recrystallized by mixed solvent recrystallization from ether/hexane to give the pure product 2-amino-5-bromophenol (0.151 g, 0.80 mmol, 60% yield; melting point 125-127 °C (decomposition), melting point reported in the literature as 149.5-150.5 °C (Boyland, E et al., 1954)). The structure of the product was confirmed by 1H NMR (CD3CN, 500 MHz) and IR (KBr): 1H NMR δ 7.08 (bs, 1H), 6.82 (d, 1H, J=2Hz), 6.78 (dd, 1H, J=8.2Hz), 6.56 (d, 1H, J=8Hz), 4.03 (bs, 2H); IR 3496 (wide) 3377, 3298, 1598, 1502, 1431, 1269, 1210, 916, 877 cm-1.

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38191-34-3
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Yield:38191-34-3 89%

Reaction Conditions:

Stage #1:N-(4-bromo-2-hydroxyphenyl)acetamide with hydrogenchloride;water in ethanol at 100; for 3 h;
Stage #2: with sodium carbonate in ethanol;water

Steps:

INTERMEDIATE B3 2-Amino-5-bromophenol A suspension of iV-(4-bromo-2-hydroxyphenyl)acetamide (Intermediate B2; 1.35 g, 5.87 mmol) in EtOH (30 mL) and 3 M HCl (30 mL) was heated to 100 ⁰C (reflux) for 3 h. To the mixture was then added 1 M Na₂CO₃ (45 mL) and the ethanol was removed under reduced pressure. The residue was extracted with DCM (3 x 250 mL), dried and concentrated. Yield 988 mg (89%). Analytical HPLC: purity 100% (System A); LRESIMS (ESI⁺) m/z = 188/190 (M+H)⁺.

References:

INOVACIA AB WO2009/150144, 2009, A1 Location in patent:Page/Page column 138

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27684-84-0 Synthesis

27684-84-0
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38191-34-3
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References

95-55-6 Synthesis