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15459-51-5

15459-51-5 Structure

15459-51-5 Structure
IdentificationBack Directory
[Name]

4-Bromo-2,6-diiodophenol
[CAS]

15459-51-5
[Synonyms]

Phenol,4-bromo-2,6-diiodo-
[Molecular Formula]

C6H3BrI2O
[MDL Number]

MFCD00672916
[MOL File]

15459-51-5.mol
[Molecular Weight]

424.8
Chemical PropertiesBack Directory
[storage temp. ]

2-8°C(protect from light)
[InChI]

InChI=1S/C6H3BrI2O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H
[InChIKey]

LFMOQCYPCSHKFH-UHFFFAOYSA-N
[SMILES]

C1(O)=C(I)C=C(Br)C=C1I
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Synthesis]

4-Bromophenol

106-41-2

4-Bromo-2,6-diiodophenol

15459-51-5

General method: Potassium iodide (2.1 eq.) was added to a 50% (v/v) aqueous solution under stirring conditions. Subsequently, a solution of acetic acid (AcOH, 1.0 M) containing 4-bromophenol (S5) and sodium percarbonate (SPC) (3.8 eq.) was slowly added over 30 min. The reaction mixture was stirred continuously at 50 °C for 2.0 h under a reflux condenser. After completion of the reaction, it was cooled to room temperature and the reaction mixture was slowly poured into a vigorously stirred two-phase mixture consisting of dichloromethane (CH2Cl2) and saturated aqueous sodium sulfite (Na2SO3) solution. The aqueous layer was separated and extracted twice with dichloromethane (CH2Cl2). The organic layers were combined and washed with saturated aqueous sodium chloride (NaCl). The organic layers were dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography to afford the target product 4-bromo-2,6-diiodophenol (23).

[References]

[1] Angewandte Chemie - International Edition, 2010, vol. 49, # 32, p. 5563 - 5566
[2] Tetrahedron, 2013, vol. 69, # 21, p. 4338 - 4352
[3] Tetrahedron Letters, 2006, vol. 47, # 28, p. 4793 - 4796
[4] Patent: WO2017/196081, 2017, A1. Location in patent: Paragraph 189; 190; 191; 192
[5] Helvetica Chimica Acta, 2011, vol. 94, # 12, p. 2248 - 2255
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