290835-85-7

Basic information

• Product Name: 2,6-Dichloro-3-fluoroacetophenone
• Synonyms: 2,6-DICHLORO-5-FLUORO ACETOPHENONE;2',6'-DICHLORO-3'-FLUOROACETOPHENONE;2,6-DICHLORO-3-FLUOROACETOPHENONE;1-(2,6-DICHLORO-3-FLUOROPHENYL)ETHANONE;2',6'-Dichloro-3'-Fluoroacetophenone 3-Fluoro-2,6-Dichloroacetophenone;2,6-dichloro-3-fluro acetophenone;2',6'-DICHLORO-3'-FLUOROACETOPHENONE, 98;2',6'-Dichloro-3'-fluoroacetophenone 98%
• CAS NO: 290835-85-7
• Molecular Formula: C₈H₅Cl₂FO
• Molecular Weight: 207.03
• Product Categories: Carbonyl Compounds;C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 290835-85-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 255 °C(lit.)
• Flash Point: 255°C
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.403 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.143mmHg at 25°C
• Refractive Index: n20/D 1.529(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,6-Dichloro-3-fluoroacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dichloro-3-fluoroacetophenone(290835-85-7)
• EPA Substance Registry System: 2,6-Dichloro-3-fluoroacetophenone(290835-85-7)

Safety Data

• Hazard Codes: Xi,F,T
• Statements: 36/37/38-22-25
• Safety Statements: 37/39-26-45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 290835-85-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liqui

Uses

Different sources of media describe the Uses of 290835-85-7 differently. You can refer to the following data:
1. 2,6-Dichloro-3-fluoroacetophenone is a halogenated derivative of Acetophenone (A164015), a reagent used in the production of fragrances and resin polymers.
2. 2′,6′-Dichloro-3′-fluoroacetophenone (2,6-Dichloro-3-fluoroacetophenone) may be used to synthesize the enantiomerically pure form of (S)-1-(2,6-dichloro-3-fluorophenyl)ethanol.

General Description

2′,6′-Dichloro-3′-fluoroacetophenone is an aryl fluorinated building block.

InChI:InChI=1/C8H5Cl2FO/c1-4(12)7-5(9)2-3-6(11)8(7)10/h2-3H,1H3

Synthetic route

1-(2,6-dichloro-3-fluorophenyl)ethanol (756520-66-8) → 2',6'-dichloro-3'-fluoroacetophenone (290835-85-7)

Conditions	Yield
With chloroamine-T; zinc dibromide In acetonitrile for 5h; Reflux;	93%

1,3-dichloro-4-fluorobenzene (1435-48-9) + acetyl chloride (75-36-5) → 2',6'-dichloro-3'-fluoroacetophenone (290835-85-7)

Conditions	Yield
With aluminum (III) chloride In dichloromethane; nitrobenzene at 20℃; for 3h;	50.7%

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → (R)-1-(2,6-dichloro-3-fluorophenyl)-1-ethanol (330156-50-8)

Conditions	Yield
With RuBr2[(R,R)-2,4-bis-(di-3,5-xylylphosphino)pentane]-(6-(p-tolyl)-2-pyridyl)methanamine; potassium tert-butylate; hydrogen In isopropyl alcohol at 40℃; under 7600.51 Torr; for 21h; Reagent/catalyst; Autoclave; Inert atmosphere;	100%
With methanol; sodium tetrahydroborate; (S)-diphenylprolinol at 5 - 20℃; for 5h; stereoselective reaction;	98.3%
With sodium tetrahydroborate; chloro-trimethyl-silane; (S)-diphenylprolinol In tetrahydrofuran at 25 - 70℃; for 1h;	95%

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → 1-(2,6-dichloro-3-fluorophenyl)ethanol (756520-66-8)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 0.666667h;	100%
Stage #1: 2',6'-dichloro-3'-fluoroacetophenone With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h; Stage #2: With hydrogenchloride In methanol; water at 0℃; pH=6;	98%
Stage #1: 2',6'-dichloro-3'-fluoroacetophenone With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h; Stage #2: With hydrogenchloride In methanol; water at 0℃; pH=6;	98%

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → (S)‐1‐(2,6-dichloro-3-fluorophenyl)ethanol (877397-65-4)

Conditions	Yield
With RuBr2[(S,S)-2,4-bis(diphenylphosphino)pentane](2-aminomethyl-3,5-dimethylpyridine); potassium tert-butylate; hydrogen In isopropyl alcohol at 40℃; for 21h; Reagent/catalyst; Concentration; Autoclave; Inert atmosphere;	100%
With RuBr2[(S,S)-2,4-bis-(di-3,5-xylylphosphino)pentane]-2-picolylamine; potassium tert-butylate; hydrogen In isopropyl alcohol at 40℃; under 7600.51 Torr; for 21h; Catalytic behavior; Reagent/catalyst; Pressure; Concentration; Time; Autoclave; Inert atmosphere;	100%
With potassium tert-butylate; hydrogen In isopropyl alcohol at 40℃; under 7600.51 Torr; for 21h; Reagent/catalyst; Autoclave; Inert atmosphere;	100%

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → (S)‐1‐(2,6-dichloro-3-fluorophenyl)ethanol (877397-65-4) + (R)-1-(2,6-dichloro-3-fluorophenyl)-1-ethanol (330156-50-8)

Conditions	Yield
With RuBr2[(S,S)-2,4-bis(diphenylphosphino)pentane](2-picolylamine); potassium tert-butylate; hydrogen In isopropyl alcohol at 40℃; for 21h; Autoclave; Inert atmosphere;	A 100% B n/a
With C33H29FeMnN2O3P(1+)*Br(1-); potassium tert-butylate; hydrogen In ethanol at 50℃; under 37503.8 Torr; for 16h; Autoclave; Overall yield = 92 %; enantioselective reaction;	A n/a B n/a
With C41H46FeMnN3O5P(1+)*Br(1-); hydrogen; potassium carbonate In ethanol at 50℃; under 37503.8 Torr; for 16h; Overall yield = 90 percent; enantioselective reaction;	A n/a B n/a
With hydrogen; C42H36FeMnN3O3P(1+)*Br(1-); potassium hydroxide In methanol at 20℃; under 22502.3 Torr; for 10h; Inert atmosphere; Glovebox; Autoclave; Overall yield = 88 percent; Overall yield = 182.2 mg; enantioselective reaction;	A n/a B n/a

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → α,α,α,2,6-pentachloro-3-fluoroacetophenone (1341170-75-9)

Conditions	Yield
Stage #1: 2',6'-dichloro-3'-fluoroacetophenone With chlorine In acetic acid at 60℃; for 5h; Stage #2: With sodium acetate In acetic acid at 60 - 100℃;	98%

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → 2,6‑dichloro‑3‑fluorobenzoic acid

Conditions	Yield
With sodium hypochlorite at 50℃; Temperature;	84%
With water; bromine; sodium hydroxide In 1,4-dioxane at -5 - 20℃; for 3h;
Stage #1: 2',6'-dichloro-3'-fluoroacetophenone With sodium hypobromide In 1,4-dioxane; water at 0 - 20℃; for 3h; Stage #2: With hydrogenchloride In 1,4-dioxane; water
Stage #1: 2',6'-dichloro-3'-fluoroacetophenone With bromine; sodium hydroxide In 1,4-dioxane; water at -5 - 20℃; Stage #2: With hydrogenchloride In 1,4-dioxane; water
With water; bromine; sodium hydroxide In 1,4-dioxane at 0 - 20℃;

amidinothiocarbamide (2114-02-5) + 2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → N-(4-(2,6-dichloro-3-fluorophenyl)-1,3-thiazol-2-yl)guanidine

Conditions	Yield
With Oxone; sodium bromide In methanol at 60℃; for 2h;	71%

2-amino-5-chlorobenzyl alcohol (37585-25-4) + 2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → 2-(2,6-dichloro-3-fluorophenyl)quinoline

Conditions	Yield
With sodium hydroxide In toluene at 135℃; for 24h; Green chemistry;	61%

4-[2-(5-ethylpyridyl)ethoxy]benzaldehyde (114393-97-4) + 2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → C24H20Cl2FNO2 (1207094-14-1)

Conditions	Yield
With sodium hydroxide In methanol at 20℃;

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → C25H21Cl2FN4O (1207094-29-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol / 20 °C 2: sodium hydroxide / methanol View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → 1-(4-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-6-(2,6-dichloro-5-fluorophenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzylidene)-1H-imidazol-5(4H)-one (1304143-30-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / methanol / 20 °C 2: sodium hydroxide / methanol 3: acetic acid / Reflux View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → methyl 2-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)-2-methylpropanoate

Conditions

Yield

Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-iodo-succinimide / acetic acid; acetonitrile / 4 h / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride / 1,2-dimethoxyethane; water / 1 h / 120 °C / Inert atmosphere; Microwave irradiation View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → 2-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)-2-methylpropanoic acid (877399-13-8)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-iodo-succinimide / acetic acid; acetonitrile / 4 h / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride / 1,2-dimethoxyethane; water / 1 h / 120 °C / Inert atmosphere; Microwave irradiation 6.1: lithium hydroxide / methanol; water / 0.75 h / 60 °C / Inert atmosphere 6.2: pH 5 / Inert atmosphere View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → C19H17Cl2FN4O3

Conditions

Yield

Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-iodo-succinimide / acetic acid; acetonitrile / 4 h / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride / 1,2-dimethoxyethane; water / 1 h / 120 °C / Inert atmosphere; Microwave irradiation View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → C18H15Cl2FN4O3

Conditions

Yield

Multi-step reaction with 6 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-iodo-succinimide / acetic acid; acetonitrile / 4 h / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride / 1,2-dimethoxyethane; water / 1 h / 120 °C / Inert atmosphere; Microwave irradiation 6.1: lithium hydroxide / methanol; water / 60 °C / Inert atmosphere 6.2: pH 5 / Inert atmosphere View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → tert-butyl 4-((4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)methyl)-4-hydroxypiperidine-1-carboxylate

Conditions

Yield

Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-iodo-succinimide / acetic acid; acetonitrile / 4 h / Inert atmosphere 5.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 1,2-dimethoxyethane; water / 85 °C / Inert atmosphere View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → tert-butyl 3-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate (877399-36-5)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-Bromosuccinimide / acetonitrile / 0.25 h / 0 °C / Inert atmosphere 5.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 1,2-dimethoxyethane; water / 85 °C / Inert atmosphere View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → C25H28Cl2FN5O3

Conditions

Yield

Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-Bromosuccinimide / acetonitrile / 0.25 h / 0 °C / Inert atmosphere 5.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 1,2-dimethoxyethane; water / 85 °C / Inert atmosphere View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → C25H28Cl2FN5O3

Conditions

Yield

Multi-step reaction with 8 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-Bromosuccinimide / acetonitrile / 0.25 h / 0 °C / Inert atmosphere 5.1: dmap / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere 6.1: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium acetate / dimethyl sulfoxide / 12 h / 80 °C / Inert atmosphere 7.1: hydrogenchloride / 1,4-dioxane; dichloromethane; water / 12 h / 40 °C / Inert atmosphere 8.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 1,2-dimethoxyethane; water / 16 h / 87 °C / Inert atmosphere View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → C26H30Cl2FN5O3

Conditions

Yield

Multi-step reaction with 8 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-Bromosuccinimide / acetonitrile / 0.25 h / 0 °C / Inert atmosphere 5.1: dmap / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere 6.1: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium acetate / dimethyl sulfoxide / 12 h / 80 °C / Inert atmosphere 7.1: hydrogenchloride / 1,4-dioxane; dichloromethane; water / 12 h / 40 °C / Inert atmosphere 8.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 1,2-dimethoxyethane; water / 16 h / 87 °C / Inert atmosphere View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → (±)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine (756521-08-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 0.67 h / 0 - 20 °C 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C 2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → (±)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine (756520-67-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 0.67 h / 0 - 20 °C 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere 3: acetic acid; iron / ethanol / 1.25 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C 2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere 3: iron; acetic acid / ethanol / 1 h / Reflux View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → (±)-5-bromo-3-(1-(2,6-dichloro-3-fluoropheny)ethoxy)pyridin-2-amine (756503-69-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-Bromosuccinimide / acetonitrile / 0.25 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / methanol / 0.67 h / 0 - 20 °C 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere 3: acetic acid; iron / ethanol / 1.25 h / Reflux 4: N-Bromosuccinimide / acetonitrile; dichloromethane / 0.17 h / 0 °C View Scheme
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C 2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere 3: iron; acetic acid / ethanol / 1 h / Reflux 4: N-Bromosuccinimide / acetonitrile / 0.25 h / 0 °C View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → 5-iodo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine (756520-48-6)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-iodo-succinimide / acetic acid; acetonitrile / 4 h / Inert atmosphere View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1H-pyrazol-1-yl)pyridin-2-amine

Conditions

Yield

Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-iodo-succinimide / acetic acid; acetonitrile / 4 h / Inert atmosphere 5.1: copper(l) iodide; potassium phosphate; dodecane / dimethyl sulfoxide / 2 h / 150 °C / Inert atmosphere; Microwave irradiation View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → N-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-pyridin-3-yl)benzamide (877620-62-7)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-iodo-succinimide / acetic acid; acetonitrile / 4 h / Inert atmosphere 5.1: copper(l) iodide; potassium phosphate; dodecane / dimethyl sulfoxide / 2 h / 150 °C / Inert atmosphere; Microwave irradiation View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → 6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-nicotinonitrile (756508-98-2)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-Bromosuccinimide / acetonitrile / 0.25 h / 0 °C / Inert atmosphere 5.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / water; N,N-dimethyl-formamide / 3 h / 100 °C / Inert atmosphere View Scheme

2',6'-dichloro-3'-fluoroacetophenone (290835-85-7) → 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-phenylpyridin-2-amine

Conditions

Yield

Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.1: iron; acetic acid / ethanol / 1 h / Inert atmosphere; Reflux 4.1: N-iodo-succinimide / acetic acid; acetonitrile / 4 h / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,2-dimethoxyethane; water / 12 h / 80 °C / Inert atmosphere View Scheme

Upstream product

• 756520-66-8 1-(2,6-dichloro-3-fluorophenyl)ethanol 
• 1435-48-9 1,3-dichloro-4-fluorobenzene 
• 75-36-5 acetyl chloride 
• 877397-65-4 (S)‐1‐(2,6-dichloro-3-fluorophenyl)ethanol 

Downstream Products

• 1207094-29-8 C₂₅H₂₁Cl₂FN₄O 
• 1304143-30-3 1-(4-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-6-(2,6-dichloro-5-fluorophenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzylidene)-1H-imidazol-5(4H)-one 
• 1341170-75-9 α,α,α,2,6-pentachloro-3-fluoroacetophenone 
• 136514-16-4 2,6-dichloro-3-fluoro-benzonitrile 
• 1413868-41-3 3-[1-(2,6-dichloro-3-fluorophenyl)-2-fluoroethyl]-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1413875-72-5 3-[1-(2,6-dichloro-3-fluorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1428476-87-2 tert-butyl 4-(4-(6-acetamido-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate 
• 1428476-70-3 N-(3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-yl)acetamide 
• 1428476-71-4 N-(3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(1-ethylpiperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-yl)acetamide 
• 1428476-72-5 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-N-ethyl-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine 
• 1428476-85-0 tert-butyl 4-(4-(5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-6-(ethylamino)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate 
• 1175296-50-0 (1S)-1-(2,6-dichloro-3-fluorophenyl)ethyl methanesulfonate 

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