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

16394-40-4
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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