161045-79-0

Usage

Uses

Used in Pharmaceutical Industry:
4-BROMO-2-CHLORO-6-FLUOROPHENOL is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties, making it a valuable component in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 4-BROMO-2-CHLORO-6-FLUOROPHENOL serves as an intermediate for the production of pesticides and other agrochemicals. Its reactivity and ability to form stable compounds contribute to the effectiveness of these products in agricultural applications.
Used in Dye Production:
4-BROMO-2-CHLORO-6-FLUOROPHENOL is utilized in the manufacturing process of dyes due to its capacity to form colored compounds. Its presence in dye molecules enhances color intensity and stability, making it suitable for various dye applications.
Used in Polymer Industry:
4-BROMO-2-CHLORO-6-FLUOROPHENOL is also employed in the production of polymers, where its reactive groups facilitate the formation of polymer chains with desired properties. Its use in polymer synthesis contributes to the development of new materials with specific characteristics for various industrial applications.
Used in Organic Compounds Synthesis:
4-BROMO-2-CHLORO-6-FLUOROPHENOL is a versatile building block in the synthesis of other organic compounds. Its reactivity allows for the formation of a wide range of organic molecules, expanding the scope of organic chemistry and enabling the creation of new compounds with diverse applications.

InChI:InChI=1/C6H3BrClFO/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H

Synthetic route

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) + chloromethyl methyl ether (107-30-2) → 5-bromo-1-chloro-3-fluoro-2-(methoxymethoxy)benzene

Conditions	Yield
With potassium carbonate In acetone at 0 - 20℃;	99%

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) + 4-bromoethylbutanoate (2969-81-5) → 4-(4-bromo-2-chloro-6-fluorophenoxy)butanoic acid ethyl ester

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h;	97%

2-chloro-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazole (913299-00-0) + 4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → 2-(4-bromo-2-chloro-6-fluorophenoxy)-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazole (1022250-06-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 96h;	16%

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → 4-bromo-2-chloro-6-fluorophenol (1401717-51-8)

Conditions	Yield
With water-d2 for 168h;

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → 2-fluoro-4-bromocyclopentadienylidenemethanone hydrochloride

Conditions	Yield
Wolff Rearrangement; UV-irradiation;

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) + Isobutyl bromide (78-77-3) → 5-bromo-1-chloro-3-fluoro-2-isobutoxybenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.5h;
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.5h;

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) + benzyl 4-isobutyl-4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide → benzyl (1-(4-bromo-2-chloro-6-fluorophenoxy)-2,4-dimethylpentan-2-yl)carbamate

Conditions	Yield
With sodium carbonate In 1-methyl-pyrrolidin-2-one at 50℃;
With sodium carbonate In 1-methyl-pyrrolidin-2-one at 50℃;

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) + bromoacetic acid methyl ester (96-32-2) → methyl 2-(4-bromo-2-chloro-6-fluorophenoxy)acetate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	2.53 g

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → C22H32ClFO5Si

Conditions

Yield

Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: titanium(IV) isopropylate / tetrahydrofuran; diethyl ether / 0 - 20 °C / Inert atmosphere 3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: 1 h / -78 - 20 °C 5.1: lithium chloride; trimethylsilyl cyanide / 2 h / 50 °C / Inert atmosphere 5.2: 0.5 h / -78 °C 5.3: 2 h / -78 °C View Scheme

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → 1-[(4-bromo-2-chloro-6-fluorophenoxy)methyl]cyclopropan-1-ol

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2: titanium(IV) isopropylate / tetrahydrofuran; diethyl ether / 0 - 20 °C / Inert atmosphere View Scheme

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → {1-[(4-bromo-2-chloro-6-fluorophenoxy)methyl]cyclopropyloxy}triethylsilane

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2: titanium(IV) isopropylate / tetrahydrofuran; diethyl ether / 0 - 20 °C / Inert atmosphere 3: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C View Scheme

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → 3-chloro-5-fluoro-4-{[1-(triethylsilyloxy)cyclopropyl]methoxy}benzaldehyde

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: titanium(IV) isopropylate / tetrahydrofuran; diethyl ether / 0 - 20 °C / Inert atmosphere 3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: 1 h / -78 - 20 °C View Scheme

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → 6-{3-chloro-5-fluoro-4-[(1-hydroxycyclopropyl)methoxy]phenyl}-5-methyl-4,5-dihydro-2H-pyridazin-3-one

Conditions

Yield

Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: titanium(IV) isopropylate / tetrahydrofuran; diethyl ether / 0 - 20 °C / Inert atmosphere 3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: 1 h / -78 - 20 °C 5.1: lithium chloride; trimethylsilyl cyanide / 2 h / 50 °C / Inert atmosphere 5.2: 0.5 h / -78 °C 5.3: 2 h / -78 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 7.1: hydrazine hydrate; acetic acid / ethanol / 8 h / Reflux View Scheme

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → methyl 4-{3-chloro-5-fluoro-4-[(1-hydroxycyclopropyl)methoxy]phenyl}-3-methyl-4-oxobutanoate

Conditions

Yield

Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: titanium(IV) isopropylate / tetrahydrofuran; diethyl ether / 0 - 20 °C / Inert atmosphere 3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: 1 h / -78 - 20 °C 5.1: lithium chloride; trimethylsilyl cyanide / 2 h / 50 °C / Inert atmosphere 5.2: 0.5 h / -78 °C 5.3: 2 h / -78 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → 5-bromo-1-chloro-2-(methoxymethoxy)-3-((2-methylallyl)oxy)benzene + 5-bromo-1-chloro-2-(methoxymethoxy)-3-((2-methylprop-1-en-1-yl)oxy)benzene

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0 - 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C View Scheme

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → 4-bromo-2-chloro-6-((2-methylallyl)oxy)phenol + 4-bromo-2-chloro-6-((2-methylprop-1-en-1-yl)oxy)phenol

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0 - 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C 2.3: 20 °C View Scheme

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → 6-bromo-8-chloro-2,2-dimethyl-2,3-dihydrobenzo[b][1,4]dioxine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0 - 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C View Scheme

4-bromo-2-chloro-6-fluoro-phenol (161045-79-0) → 8-chloro-6-iodo-2,2-dimethyl-2,3-dihydrobenzo[b][1,4]dioxine

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 0 - 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C 3.1: trans-1,2-cyclohexanediamine; sodium iodide; copper(l) iodide / 1,4-dioxane / 115 °C / Inert atmosphere View Scheme

Downstream Products

• 1022250-06-1 2-(4-bromo-2-chloro-6-fluorophenoxy)-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazole 
• 1401717-51-8 4-bromo-2-chloro-6-fluorophenol