626-02-8

Usage

Uses

Used in Organic Synthesis:
3-Iodophenol is used as a chemical intermediate for esterification, which allows for the formation of esters that can be used in various applications, such as pharmaceuticals, agrochemicals, and fragrances.
Used in Electrophilic Aromatic Substitution:
3-Iodophenol is used as a substrate in electrophilic aromatic substitution reactions, which are essential for the synthesis of various organic compounds, including dyes, plastics, and pharmaceuticals.
Used in Alkylation:
3-Iodophenol is used as a reactant in alkylation reactions, which involve the introduction of an alkyl group to the phenol molecule. This process is crucial for the production of various organic compounds, such as alkylphenols and their derivatives.
Used in Nucleophilic Aromatic Substitution:
3-Iodophenol is used as a substrate in nucleophilic aromatic substitution reactions, which are important for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and dyes.
Used in Mitsunobu Reactions:
3-Iodophenol is used as a reactant in Mitsunobu reactions, which are a class of organic reactions that involve the conversion of alcohols to their corresponding esters or ethers. This process is useful for the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Transition Metal-Catalyzed Cross-Coupling:
3-Iodophenol is used as a reactant in transition metal-catalyzed cross-coupling reactions, which are essential for the formation of carbon-carbon bonds in various organic compounds. This process is crucial for the synthesis of complex organic molecules, such as pharmaceuticals, agrochemicals, and advanced materials.
Used in Acylation:
3-Iodophenol is used as a reactant in acylation reactions, which involve the introduction of an acyl group to the phenol molecule. This process is important for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and dyes.
Used in Oxidation Reactions:
3-Iodophenol is used as a substrate in oxidation reactions, which are essential for the synthesis of various organic compounds, including quinones, phenolic acids, and other oxidized derivatives. These compounds have applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

Synthesis

3-Iodophenol Synthesis:1）Add potassium tert-butoxide (67.3 mg, 0.60 mmol, 2.0 eq.), oxime (74.5 mg, 0.60 mmol, 2.0 eq.), and 4′-bromoacetophenone (59.7 mg, 0.30 mmol, 1.0 eq.) to an oven-dry screw-cap 8mL reaction vial.2）Add anhydrous DMSO (1.5 mL) to the solids a magnetic stir bar.3）Close the vial and sparge the reaction mixture with N2 for 15 minutes, seal with parafilm.4）Stir the reaction mixture and heat at 100°C in a metal heating block for 16 h.5）Dilute the mixture with CH2Cl2 or EtOAc (20 mL), pour into a mixture of water (10mL) and brine (5 mL), acidify with 10% aq HCl (~1 mL).6）Collect the organic phase and extract the aqueous phase with CH2Cl2 or EtOAc (3×20mL).7）Combine the organics, dry (MgSO4) and concentrate under reduced pressure.8）Purify the crude product to give 3-Iodophenol by column chromatography (30% EtOAc in hexane).

InChI:InChI=1/C6H5IO/c7-5-2-1-3-6(8)4-5/h1-4,8H

Upstream product

• 766-85-8 3-methoxy-1-iodobenzene 
• 111-92-2 dibutylamine 
• 81577-20-0 Carbonic acid butyl ester 3-iodo-phenyl ester 
• 64-17-5 ethanol 
• 66416-73-7 p-hydroxy-o-iodoaniline 
• 763084-51-1 (2Z)-2-(3-iodophenoxy)but-2-enoic acid 
• 626-00-6 1,3-Diiodobenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 138769-92-3 cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene 
• 107623-21-2 1-(benzyloxy)-3-iodobenzene 
• 1878-93-9 (3-iodophenoxy)acetic acid 
• 133910-12-0 (1,1-dimethylethyl)(3-iodophenoxy)dimethylsilane 
• 111-86-4 n-Octylamine 
• 591-27-5 m-Hydroxyaniline 

Downstream Products

• 90888-05-4 2-(3-Iod-phenoxy)-buttersaeure 
• 38170-02-4 4-iodosalicylaldehyde 
• 90151-01-2 4-hydroxy-2-iodobenzaldehyde 
• 107623-21-2 1-(benzyloxy)-3-iodobenzene 
• 766-85-8 3-methoxy-1-iodobenzene 
• 15286-24-5 p-Hydroxyphenyldimethylphosphonat 
• 612-76-0 1,1'-biphenyl-3,3'-diol 
• 141090-47-3 1-propyl-3-(3-hydroxyphenyl)-1,2,3,6-tetrahydropyridine 
• 133910-12-0 (1,1-dimethylethyl)(3-iodophenoxy)dimethylsilane 
• 10540-41-7 4'-fluoro-[1,1'-biphenyl]-3-ol 
• 398-23-2 4,4'-difluorobiphenyl 
• 38169-97-0 2-hydroxy-6-iodobenzaldehyde 
• 153688-92-7 3-iodophenyl trifluoromethanesulfonate 
• 819059-98-8 3-iodophenyl 2-formylphenyl ether 

Relevant academic research and scientific papers

Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions

Phenols are extremely valuable building blocks in the areas of pharmaceuticals, natural products, materials and catalysts. In order to carry out modifications on phenols, the phenolic oxygen is routinely protected to prevent unwanted side reactions. Presently many of the protecting groups available can require harsh conditions, specialist equipment, expensive or air/moisture-sensitive reagents to install and remove. Here we introduce the use of the tetrafluoropyridyl (TFP) group as a general protecting group for phenols. TFP can be installed in one step with no sensitivity to water or air, and it is stable under a range of commonly employed reaction conditions including acid and base. The TFP protecting group is readily cleaved under mild conditions with quantitative conversion to the parent phenol, observed in many cases in less than 1 hour.

A process for the preparation of key intermediate lei meiti amine, its preparation and use

The invention discloses critical intermediates (with the structure formula (I) ) used for preparing ramelteon. In the formula (I), A is O or S; R is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, n-pentyl, isopentyl, cyclopentyl, phenyl, benzyl or p-methoxybenzyl; and when chiral carbon exists, the chemical compounds in the formula (I) are racemate or optically active compounds. When the A in the formula (I) is O and the R in the formula (I) is ethyl, the chemical compound is the chemical compound shown as the structure formula (II). In addition, the invention further discloses a preparing method of the chemical compound shown as the formula (II) and applications of the formula (II) in preparation of the ramelteon used for treating insomnia.

Method for continuous flow synthesis of phenol-based compound

The present invention provides a method for continuous flow synthesis of a phenol-based compound represented by a formula (III), wherein the method is performed in two static mixers, a tubular reactor and an oil-water separator, wherein the two static mixers, the tubular reactor and the oil-water separator are sequentially connected in series. The method comprises that an acid solution and an aniline compound represented by a formula (I) are pumped into the static mixer A; the mixture of the acid solution and the compound represented by the formula (I) flows out from the static mixer A and flows into the static mixer B connected to the static mixer A; a sodium nitrite solution is pumped into the static mixer B, and a reaction is performed to produce a diazonium salt solution represented by a formula (II); and the solution represented by the formula (II) flows out from the static mixer B, is pumped into the tubular reactor connected to the static mixer B, and then into the oil-water separator connected to the tubular reactor, and the water phase is separated to obtain the compound represented by the formula (III). According to the present invention, the method has characteristics of short reaction time, solvent saving and high yield, and can well solve the problems in the synthesis of the phenol-based compound through diazotization hydrolysis in the intermittent kettle type reactor. The formulas (I), (II) and (III) are defined in the specification.

Thermal Protodeboronation of hydroxyarene Boronic Acids and Its Application to ortho- and meta- Functionalization of hydroxyarene Using Boronic Acids as Blocking and Directing Groups

The present invention refers to hydroxy arene boron acid compounds that thermal de borohydride of phenolic compounds using functional groups in ortho-or meta-position with hydroxy [...] manufacturing method relates to, more particularly boron position and outputs ortho of phenol then substituted acid, ortho-or meta-position boron arene hydroxy then introduced to a functional groups in making and compounds, thermal de using borohydride said boron acid by removing phenol from ortho-or meta-position functional groups in have been introduced method for preparing the compounds of arene hydroxy relates to. Manufacturing method of arene compound hydroxy the present invention according to such as iridium or a palladium metal catalyst-free, a stronger acid than the acid or base conditions, a low-temperature reaction acid and acetic anhydride the microbeam generating reactions, by causing or permitting a condition without requiring a step of client and, simply phenol from ortho-or meta-position for introducing functional groups to hydroxy arene compound can be produced.

Continuous-flow hydroxylation of aryl iodides promoted by copper tubing

A simple and ligand-free synthesis of phenols from the corresponding aryl iodides in a continuous-flow system is described. The reaction is complete in only 4 to 20 minutes when heated between 150 to 165 °C in a reactor consisting of a commercially available copper coil. An example of trapping of the phenoxide in situ is also shown.

Synthesis of the melatonin receptor agonist Ramelteon using a tandem C-H activation-alkylation/Heck reaction and subsequent asymmetric Michael addition

An asymmetric synthesis of the melatonin receptor agonist Ramelteon 1 has been achieved, which involved a tandem C-H activation-alkylation/Heck reaction and subsequent highly diastereoselective asymmetric Michael addition to generate the corresponding chiral intermediate, which was readily converted into Ramelteon 1 in 19% overall yield in 15 linear steps.

Protodeboronation of ortho- and para-phenol boronic acids and application to ortho and meta functionalization of phenols using boronic acids as blocking and directing groups

The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by σ-bond metathesis.

Base-catalyzed dehydration of 3-substituted benzene cis -1,2-dihydrodiols: Stabilization of a cyclohexadienide anion intermediate by negative aromatic hyperconjugation

Evidence that a 1,2-dihydroxycyclohexadienide anion is stabilized by aromatic "negative hyperconjugation" is described. It complements an earlier inference of "positive" hyperconjugative aromaticity for the cyclohexadienyl cation. The anion is a reactive intermediate in the dehydration of benzene cis-1,2-dihydrodiol to phenol. Rate constants for 3-substituted benzene cis-dihydrodiols are correlated by σ- values with = 3.2. Solvent isotope effects for the reactions are kH2O/kD 2O = 1.2-1.8. These measurements are consistent with reaction via a carbanion intermediate or a concerted reaction with a "carbanion-like" transition state. These and other experimental results confirm that the reaction proceeds by a stepwise mechanism, with a change in rate-determining step from proton transfer to the loss of hydroxide ion from the intermediate. Hydrogen isotope exchange accompanying dehydration of the parent benzene cis-1,2-dihydrodiol was not found, and thus, the proton transfer step is subject to internal return. A rate constant of ～1011 s-1, corresponding to rotational relaxation of the aqueous solvent, is assigned to loss of hydroxide ion from the intermediate. The rate constant for internal return therefore falls in the range 1011-1012 s -1. From these limiting values and the measured rate constant for hydroxide-catalyzed dehydration, a pKa of 30.8 ± 0.5 was determined for formation of the anion. Although loss of hydroxide ion is hugely exothermic, a concerted reaction is not enforced by the instability of the intermediate. Stabilization by negative hyperconjugation is proposed for 1,2-dihydroxycyclohexadienide and similar anions, and this proposal is supported by additional experimental evidence and by computational results, including evidence for a diatropic ("aromatic") ring current in 3,3-difluorocyclohexadienyl anion.

Mild debenzylation of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene as a non-lewis-basic cation scavenger

Scope and limitations of the debenzylation conditions for aryl benzyl ether, which was developed during our synthetic studies on yatakemycin, were investigated. The chemoselective debenzylation proceeds at low temperature with a combination of BCl3 and pentamethylbenzene as a cation scavenger in the presence of various functional groups.

High-yielding cleavage of (aryloxy)acetates

A reliable and high-yielding one-pot sequence for the removal of O-carboxymethyl moieties from phenols is presented. When diethylphosphoryl azide is employed as the azide transfer reagent in the Curtius rearrangement and glycerol in the subsequent hydrolytic workup, the protocol can be reliably applied to a very broad scope of substrates. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.