24155-42-8

Basic information

• Product Name: alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol
• Synonyms: 1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)ETHANOL;1-(2,4-dichlorophenyl)-2-(1-imidazolyl)ethanol;1-(2,4-DICHLOROPHENYL)-2-IMIDAZOL-1-YL ETHANOL;1H-IMIDAZOLE-1-ETHANOL, ALPHA-(2,4-DICHLOROPHENYL)-;ALPHA-(2,4-DICHLOROPHENYL)-1H-IMIDAZOLE-1-ETHANOL;ALPHA-(2,4-DICHLOROPHENYL)-2-1H-IMIDAZOLE-1-ETHANOL;ALPHA-(2,4-DICHLORO PHENYL)-B-(IMIDAZOLE-YL)ETHANOL;-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol
• CAS NO: 24155-42-8
• Molecular Formula: C₁₁H₁₀Cl₂N₂O
• Molecular Weight: 257.12
• EINECS: 246-042-5
• Product Categories: Imidazol&Benzimidazole;Imidazoles;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 24155-42-8.mol
• Article Data: 27

Chemical Properties

• Melting Point: 134-138 °C
• Boiling Point: 468.5 °C at 760 mmHg
• Flash Point: 237.1 °C
• Appearance: White to light pink crystal
• Density: 1.4133 (rough estimate)
• Vapor Pressure: 1.41E-09mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.25±0.20(Predicted)
• Water Solubility: 1300 g/L (20 ºC)
• CAS DataBase Reference: alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol(24155-42-8)
• EPA Substance Registry System: alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol(24155-42-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 38-28B-36-26
• WGK Germany: 3
• RTECS: NI5485000
• Hazardous Substances Data: 24155-42-8(Hazardous Substances Data)

Usage

Chemical Properties

cream-coloured to beige powder

Uses

Intermediate in the preparation of Miconazole. An impurity in the synthesis of Fenticonazole. An impurity in the synthesis of Ketoconazole.

Uses

Intermediate in the preparation of Miconazole.An impurity in the synthesis of Fenticonazole.An impurity in the synthesis of Ketoconazole.Econazole EP Impurity A.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C11H10Cl2N2O/c12-8-1-2-9(10(13)5-8)11(16)6-15-4-3-14-7-15/h1-5,7,11,16H,6H2/t11-/m0/s1

Synthetic route

1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone (46503-52-0) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 12h;	98%
With potassium borohydride In methanol for 1h; Reflux;	90.5%
With sodium tetrahydroborate In methanol for 2h; Reflux;	88%

1H-imidazole (288-32-4) + α-(chloromethyl)-2,4-dichlorobenzyl alcohol (13692-14-3) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8)

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; alumina-supported potassium hydroxide at 45℃; for 3.5h;	90%
With potassium carbonate; sodium iodide In water; butanone	78.7%
With sodium In N-methyl-acetamide; methanol; water

1H-imidazole (288-32-4) + 2-(2,4-dichlorophenyl)oxirane (13692-15-4) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8)

Conditions	Yield
With pyridine In ethanol for 12h; Ring cleavage; Heating;	63%
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: 2-(2,4-dichlorophenyl)oxirane In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	57%
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide Inert atmosphere; Stage #2: 2-(2,4-dichlorophenyl)oxirane In N,N-dimethyl-formamide at 20℃; Inert atmosphere;

tetra-n-butylammonium imidazolate (67035-78-3) + α-(chloromethyl)-2,4-dichlorobenzyl alcohol (13692-14-3) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8)

Conditions	Yield
In acetonitrile Reflux;	68%

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanone nitrate → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8)

Conditions	Yield
With sodium tetrahydroborate In methanol for 2h;	95%

tetra-n-butylammonium imidazolate (67035-78-3) + 2-bromo-1-(2,4-dichlorophenyl)ethanol (53066-15-2) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8)

Conditions	Yield
In acetonitrile Reflux;	40%

2,2',4'-trichloroacetophenone (4252-78-2) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 28 percent / CH2Cl2 / 2 h / 40 °C 2: sodium borohydride View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / isopropyl alcohol / 2 h / 3 - 20 °C 2: acetonitrile / Reflux View Scheme
Multi-step reaction with 2 steps 1: dichloromethane 2: potassium borohydride / methanol / 1 h / Reflux View Scheme

2,4-dichlorophenacyl bromide (2631-72-3) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / isopropyl alcohol / 2 h / 3 - 20 °C 2: acetonitrile / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide; water / 20 °C 2: sodium tetrahydroborate / methanol / 2 h / 5 - 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / 20 °C 2: sodium tetrahydroborate / methanol / 2 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / tetrahydrofuran / 3 h / 20 °C 2: sodium tetrahydroborate / methanol / 3 h / 0 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 2: sodium tetrahydroborate; methanol / 2 h / 0 °C / Reflux View Scheme

1,3-Dichlorobenzene (541-73-1) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / 3 h / 30 °C 2.1: triethylamine / methanol / 20 °C 2.2: 4 h / 65 °C 3.1: sodium tetrahydroborate / ethanol / 12 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride 2: triethylamine / methanol / 65 °C 3: sodium tetrahydroborate / ethanol / 20 °C View Scheme

1-(2,4-dichlorophenyl)ethan-1-one (2234-16-4) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine / chloroform / 1.5 h / 0 - 20 °C 2: potassium carbonate / 20 °C 3: sodium tetrahydroborate / methanol / 2 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: bromine / chloroform / 1 h / 0 - 20 °C 2: potassium carbonate / tetrahydrofuran / 3 h / 20 °C 3: sodium tetrahydroborate / methanol / 3 h / 0 °C / Reflux View Scheme
Multi-step reaction with 3 steps 1: bromine / chloroform / 1 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C 3: sodium tetrahydroborate; methanol / 2 h / 0 °C / Reflux View Scheme

2,2',4'-trichloroacetophenone (4252-78-2) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) + n-butyl halide

Conditions	Yield
Multi-step reaction with 2 steps 1: acetonitrile 2: NaBH4 / ethanol View Scheme

2,4-dichlorobenzaldeyhde (874-42-0) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium hydroxide / acetonitrile; water / 3 h / 60 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2.2: 60 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: potassium hydroxide / acetonitrile / 60 - 65 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere 2.2: 20 °C / Inert atmosphere View Scheme

2,4-dichlorophenacyl bromide (2631-72-3) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) + n-butyl halide

Conditions	Yield
Multi-step reaction with 2 steps 1: CHCl3 / 0 °C 2: sodium borohydride / ethanol / 4 h / Heating View Scheme

2,4-dichlorobenzaldeyhde (874-42-0) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) + 3,4-Cl2-C6H3-SO2CH2-X, (X=Cl or Br)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / aq. KOH / acetonitrile / 3 h / 60 °C 2: 63 percent / pyridine / ethanol / 12 h / Heating View Scheme

Hexanoyl chloride (142-61-0) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → 1-[2,4-dichloro-β-(n-pentylcarbonyloxy)phenethyl]imidazole

Conditions	Yield
With triethylamine In dichloromethane for 4h; Ambient temperature;	97%

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) + 2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (16977-78-9, 85193-55-1, 86651-32-3, 86651-40-3) → 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide

Conditions	Yield
In acetonitrile at 110℃;	96%
In acetonitrile at 110℃; for 24h;	90%

3-Bromomethyl-7-chlorobenzothiophene (17512-61-7) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → sertaconazole nitrate (99592-39-9)

Conditions	Yield
Stage #1: 3-Bromomethyl-7-chlorobenzothiophene; 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutyl-ammonium chloride; sodium hydroxide In water; toluene at 80℃; for 4h; Stage #2: With nitric acid	95.7%

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) + 3-chloroprop-1-ene (107-05-1) → 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole (35554-44-0)

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With potassium hydroxide In water; dimethyl sulfoxide at 20℃; for 1h; Stage #2: 3-chloroprop-1-ene In water; dimethyl sulfoxide at 30℃; for 3h; Solvent; Temperature;	95.6%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With potassium hydroxide In water; dimethyl sulfoxide at 20 - 35℃; for 1h; Stage #2: 3-chloroprop-1-ene In water; dimethyl sulfoxide at 35 - 40℃; Reagent/catalyst;	68%

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) + n-octanoic acid chloride (111-64-8) → 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-1-octanoyloxy-ethane (68571-21-1)

Conditions	Yield
With triethylamine In dichloromethane for 4h; Ambient temperature;	95%

n-decanoyl chloride (112-13-0) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → 1-[2,4-dichloro-β-(n-nonylcarbonyloxy)phenethyl]imidazole

Conditions	Yield
With triethylamine In dichloromethane for 4h; Ambient temperature;	91%

acetic anhydride (108-24-7) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl acetate (61258-54-6)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 1.5h; Inert atmosphere;	91%

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → (±)-1-(2-azido-2-(2, 4-dichlorophenyl)ethyl)-1H-imidazole (94038-18-3)

Conditions	Yield
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 0 - 20℃; for 3.25h; Inert atmosphere;	87%
With diazabicycloundecane; diphenyl phosphoryl azide In tetrahydrofuran
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide

3-(bromomethyl)benzothiophene (1196-19-6) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → 1-(2-(benzo[b]thiophen-3-ylmethoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole (99592-24-2)

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h; Stage #2: 3-(bromomethyl)benzothiophene In toluene for 3h; Heating;	86%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h; Stage #2: 3-(bromomethyl)benzothiophene In toluene for 3h; Heating;	86%
With sodium hydride 1.) HMPT, RT; 2.) HMPT, 50 deg C, 1 h, 3.) HMPT, 0 deg C, 5 h;; Multistep reaction;

1-phenylthio-4-chloromethyl-benzene (1208-87-3) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → α-(2,4-dichlorophenyl)-β,N-imidazolylethyl 4-phenylthiobezyl ether nitrate

Conditions	Yield
Stage #1: 1-phenylthio-4-chloromethyl-benzene; 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 58 - 60℃; for 13.5h; Stage #2: With nitric acid In ethyl acetate; toluene at 25℃; for 3h;	85.1%
Stage #1: 1-phenylthio-4-chloromethyl-benzene; 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydroxide In tetrahydrofuran; water for 4.5h; Stage #2: With nitric acid In water	82.1%
Stage #1: 1-phenylthio-4-chloromethyl-benzene; 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 58℃; for 13.5h; Stage #2: With nitric acid In ethyl acetate; toluene at 25℃; for 3h;	74.7%
Stage #1: 1-phenylthio-4-chloromethyl-benzene; 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 58 - 60℃; for 13.5h; Stage #2: With nitric acid In ethyl acetate at 25℃; for 3h;	71.4%

Nonanoyl chloride (764-85-2) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → 1-[2,4-dichloro-β-(n-octylcarbonyloxy)phenethyl]imidazole

Conditions	Yield
With triethylamine In dichloromethane for 4h; Ambient temperature;	84%

propionyl chloride (79-03-8) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → Propionic acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester

Conditions	Yield
With triethylamine In dichloromethane for 4h; Ambient temperature;	83%

n-dodecanoyl chloride (112-16-3) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → 1-(2,4-dichloro-phenyl)-1-dodecanoyloxy-2-imidazol-1-yl-ethane (68571-23-3)

Conditions	Yield
With triethylamine In dichloromethane for 4h; Ambient temperature;	82%

undecanoyl chloride (17746-05-3) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → Undecanoic acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester

Conditions	Yield
With triethylamine In dichloromethane for 4h; Ambient temperature;	82%

trans-geranyl bromide (6138-90-5) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → 1-[2-(2,4-dichlorophenyl)-2-((E)-3,7-dimethylocta-2,6-dienyloxy)ethyl]-1H-imidazole

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In N,N-dimethyl-formamide at 40℃; for 0.5h; deprotonation; Stage #2: trans-geranyl bromide In N,N-dimethyl-formamide at 20℃; for 0.5h; Etherification;	82%
In N-methyl-acetamide

7-chloro-3-(chloromethyl)benzo[b]thiophene + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → sertaconazole (99592-32-2)

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetra-(n-butyl)ammonium iodide; sodium hydroxide In water; toluene at 50℃; for 0.25h; Inert atmosphere; Stage #2: 7-chloro-3-(chloromethyl)benzo[b]thiophene In water; toluene at 50℃; for 4h; Inert atmosphere;	82%

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) + 2-(bromomethyl)naphthalene (3163-27-7) → 1-(2-(2,4-dichlorophenyl)-2-(naphthalen-1-ylmethoxy)ethyl)-1H-imidazole

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; tetra-(n-butyl)ammonium iodide; sodium hydride at 0℃;	80%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h; Stage #2: 2-(bromomethyl)naphthalene In toluene for 3h; Heating;	72%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h; Stage #2: 2-(bromomethyl)naphthalene In toluene for 3h; Heating;	72%

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) + 2-bromomethylnaphthyl bromide (939-26-4) → 1-(2-(2,4-dichlorophenyl)-2-(naphthalen-2-ylmethoxy)ethyl)-1H-imidazole

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h; Stage #2: 2-bromomethylnaphthyl bromide In toluene for 3h; Heating;	76%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h; Stage #2: 2-bromomethylnaphthyl bromide In toluene for 3h; Heating;	76%
With sodium hydride 1.) HMPA, 20 degC - 25 degC, 1 h; 50 degC - 60 degC, 2 h; 2.) 50 degC, 20 h; Yield given. Multistep reaction;

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → 1-chloro-1-(2,4-dichlorophenyl)-2-(1H-imidazole-1-yl)ethane (46503-49-5)

Conditions	Yield
With thionyl chloride at 20℃; for 12h;	74.3%
With thionyl chloride In dichloromethane
With thionyl chloride at 20℃;

butyryl chloride (141-75-3) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → Butyric acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester

Conditions	Yield
With triethylamine In dichloromethane for 4h; Ambient temperature;	74%

2,4-Dichlorobenzyl chloride (94-99-5) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → miconazole (22916-47-8)

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Substitution; Stage #2: 2,4-Dichlorobenzyl chloride In tetrahydrofuran at 45℃; for 16h; Substitution;	73%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In N,N-dimethyl-formamide Inert atmosphere; Stage #2: 2,4-Dichlorobenzyl chloride In N,N-dimethyl-formamide at 20℃;

p-phenylbenzyl bromide (2567-29-5) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → 1-[2-biphenyl-4-ylmethoxy-2-(2,4-dichloro-phenyl)-ethyl]-1H-imidazole (73151-17-4)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; tetra-(n-butyl)ammonium iodide; sodium hydride at 0℃;	73%

n-valeryl chloride (638-29-9) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → Pentanoic acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester

Conditions	Yield
With triethylamine In dichloromethane for 4h; Ambient temperature;	71%

3-Bromomethylthiophene (34846-44-1) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → 1-(2-(2,4-dichlorophenyl)-2-(thiophen-3-ylmethoxy)ethyl)-1H-imidazole (119386-74-2)

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h; Stage #2: 3-Bromomethylthiophene In toluene for 3h; Heating;	71%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h; Stage #2: 3-Bromomethylthiophene In toluene for 3h; Heating;	71%

1,3-Dichloro-2-chloromethyl-benzene (2014-83-7) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → isoconazole

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In 1,4-dioxane; mineral oil at 20℃; for 1h; Inert atmosphere; Reflux; Stage #2: 1,3-Dichloro-2-chloromethyl-benzene In 1,4-dioxane; mineral oil Inert atmosphere; Reflux;	70%

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) + 4-bromobenzyl halide → 1-(2-((4-bromobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In N,N-dimethyl-formamide at -5 - 20℃; for 1.5h; Inert atmosphere; Stage #2: 4-bromobenzyl halide In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere;	68.4%

Upstream product

• 241-55-4 indolo(3,2-b)carbazole 
• 24155-39-3 1-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-imidazol-1-ium nitrate 
• 24155-34-8 2-(1H-imidazol-1-yl)-1-phenylethanone 
• 24155-32-6 1-(4-CHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)-1-ETHANONE 
• 24155-31-5 1-[2-(2-chlorophenyl)-2-oxoethyl]-1H-imidazol-1-ium nitrate 
• 24155-30-4 1-(4-BROMOPHENYL)-2-(1H-IMIDAZOL-1-YL)-1-ETHANONE 
• 24155-29-1 1-[2-(2,4-dichlorophenyl)-2-oxoethyl]-1H-imidazole mononitrate 
• 24154-37-8 2,4,6-TRIIODO-PHENYLAMINE 
• 2415-43-2 URIDYLYL-(3',5')-URIDINE 
• 24154-26-5 2,5-DIHYDROXYPYRIDINE 
• 24154-09-4 Phosphoric acid 4-bromophenyl ester 
• 24154-06-1 (1-chloroethenyl)cyclopropane 
• 24153-72-8 1-butanone, 1-[2,4,6-tris(1-methylethyl)-3-nitrophenyl]- 
• 24153-71-7 1-butanone, 1-[2,4,6-tris(1-methylethyl)phenyl]- 

Downstream Products

• 35554-44-0 Imazalil 

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