204205-33-4

Basic information

• Product Name: 2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone
• Synonyms: Prasugrel Intermediate 4;2-Bromo-2-(2-fluorophenyl);Ethanone, 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)-;2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone;Cylopropylcarbonyl-2-flurobenzyl bromide;2-Bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone;Chemical intermediate for Prasugrel;2-broMo-1-cyclopropyl-2-(2-fluorophenyl)ethan-1-one
• CAS NO: 204205-33-4
• Molecular Formula: C₁₁H₁₀BrFO
• Molecular Weight: 257.1
• EINECS: 1806241-263-5
• Mol File: 204205-33-4.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 293.012 °C at 760 mmHg
• Flash Point: 131.009 °C
• Appearance: /
• Density: 1.574 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone(204205-33-4)
• EPA Substance Registry System: 2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone(204205-33-4)

Safety Data

• Hazardous Substances Data: 204205-33-4(Hazardous Substances Data)

Usage

Uses

2-?Bromo-?2-?(2-?fluorophenyl)?-?1-?cyclopropylethanone is a reagent used in the synthesis of potent anti-oxidant agents.

InChI:InChI=1/C11H10BrFO/c12-10(11(14)7-5-6-7)8-3-1-2-4-9(8)13/h1-4,7,10H,5-6H2

Synthetic route

1-cyclopropyl-2-(2-fluorophenyl)ethanone (150322-73-9) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
With iodine(I) bromide; 1-n-butyl-3-methylimidazolim bromide In tetrahydrofuran at 40℃; for 4h; Temperature; Time; Concentration;	95.3%
With bromine In methanol at 25 - 30℃; for 6h; Concentration;	94.65%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile) In cyclohexane at 10℃; Product distribution / selectivity; Reflux;	93.28%

(2-fluorophenyl)acetic acid (451-82-1) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.25 h / 0 - 5 °C 1.2: 6 h / 0 - 5 °C 2.1: iodine; magnesium / tetrahydrofuran / 25 - 50 °C 2.2: 40 - 50 °C 2.3: 0.25 h / 0 - 30 °C 3.1: toluene-4-sulfonic acid; 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 4 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 1.2: 5 - 65 °C 2.1: dibenzoyl peroxide; N-Bromosuccinimide / ethyl acetate / 25 - 60 °C View Scheme
Multi-step reaction with 2 steps 1.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 1.2: 5 - 65 °C 2.1: dibenzoyl peroxide; N-Bromosuccinimide / ethyl acetate / 25 - 60 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / toluene; dimethyl sulfoxide / 1.5 h / 95 - 110 °C / Large scale 2: bromine / methanol / Large scale View Scheme

2-(2-fluorophenyl)-N-methoxy-N-methylacetamide (946402-23-9) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: iodine; magnesium / tetrahydrofuran / 25 - 50 °C 1.2: 40 - 50 °C 1.3: 0.25 h / 0 - 30 °C 2.1: toluene-4-sulfonic acid; 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 4 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: iodine; magnesium / tetrahydrofuran / 40 - 50 °C 1.2: 0.25 h / 0 - 30 °C 2.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / toluene-4-sulfonic acid / dichloromethane / 4.75 h / 0 - 5 °C / Reflux View Scheme

2-fluorobenzyl chloride (345-35-7) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: tetrabutylammomium bromide / dichloromethane; water / 25 °C 2.1: sodium hydroxide; water / 5 - 95 °C 2.2: pH 2 - 3 3.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 3.2: 5 - 65 °C 4.1: dibenzoyl peroxide; N-Bromosuccinimide / ethyl acetate / 25 - 60 °C View Scheme
Multi-step reaction with 4 steps 1.1: tetrabutylammomium bromide / dichloromethane; water / 25 °C 2.1: sodium hydroxide; water / 5 - 95 °C 2.2: pH 2 - 3 3.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 3.2: 5 - 65 °C 4.1: dibenzoyl peroxide; N-Bromosuccinimide / ethyl acetate / 25 - 60 °C View Scheme
Multi-step reaction with 2 steps 1: magnesium; iodine / tetrahydrofuran; 2-methyltetrahydrofuran / 1.5 h / 40 - 45 °C / Inert atmosphere 2: N-Bromosuccinimide; toluene-4-sulfonic acid / acetonitrile / 24 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: magnesium; iodine / tetrahydrofuran; toluene / 1.5 h / 40 - 45 °C / Inert atmosphere 2: N-Bromosuccinimide; toluene-4-sulfonic acid / acetonitrile / 24 h / 40 °C View Scheme

2-fluorophenyl acetonitrile (326-62-5) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / 5 - 95 °C 1.2: pH 2 - 3 2.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 2.2: 5 - 65 °C 3.1: dibenzoyl peroxide; N-Bromosuccinimide / ethyl acetate / 25 - 60 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / 5 - 95 °C 1.2: pH 2 - 3 2.1: magnesium; isopropyl bromide / toluene; tetrahydrofuran / 15 - 65 °C 2.2: 5 - 65 °C 3.1: dibenzoyl peroxide; N-Bromosuccinimide / ethyl acetate / 25 - 60 °C View Scheme

ethyl cyclopropylcarboxylate (4606-07-9) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Stage #1: With iodine; magnesium; isopropyl bromide In tetrahydrofuran at 65℃; for 3h; Stage #2: ethyl cyclopropylcarboxylate In tetrahydrofuran at 5 - 70℃; for 3.16667h; Stage #3: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid In chloroform at 28 - 65℃; for 4h;

2-(2-fluorophenyl acetic acid) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / dicyclohexyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 6 h / 0 - 5 °C 2.1: iodine; magnesium / tetrahydrofuran / 40 - 50 °C 2.2: 0.25 h / 0 - 30 °C 3.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / toluene-4-sulfonic acid / dichloromethane / 4.75 h / 0 - 5 °C / Reflux View Scheme

fluorobenzene (462-06-6) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: tin(IV) chloride / tetrahydrofuran / 4 h / 45 °C 2: dichloromethane / 4 h / 20 °C 3: bromine / tetrahydrofuran / 10 h / 20 °C View Scheme

methyl o-fluorophenylacetate (57486-67-6) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / tetrahydrofuran / 6 h / 20 - 60 °C 2: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 8 h / 20 °C View Scheme

o-fluorobenzyl bromide (446-48-0) → 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium / methyl iodide / diethyl ether / 20 °C 1.2: 20 °C 1.3: 0 °C 2.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile) / cyclohexane / 10 °C / Reflux View Scheme

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one (150322-38-6)

Conditions	Yield
With ammonium bicarbonate In dichloromethane at 5 - 20℃;	98%
With copper(l) iodide; sodium carbonate; XPhos In 1,4-dioxane at 60℃; for 3h; Reagent/catalyst; Temperature; Inert atmosphere;	90.2%
With potassium phosphate; iodine In 1,4-dioxane at 80℃; for 4h; Temperature; Time; Reagent/catalyst;	87.6%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + N-allyl isothiocyanate (57-06-7) + 4-aminoethylbenzene (589-16-2) → 3-allyl-2-(4'-ethylphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 18h; regioselective reaction;	96%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1h; regioselective reaction;	96%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 2-[1-(2-naphthenyl)ethyledene]hydrazinecarbothioamide (133477-39-1) → 4-cyclopropyl-5-(2-fluorophenyl)-2-((1-(naphthalen-2-yl)ethylidene)hydrazono)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.333333h; Hantzsch Thiazole Synthesis; Reflux;	96%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + p-toluidine (106-49-0) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-methylphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 20h; Reagent/catalyst; Temperature; Time; regioselective reaction;	95%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1h; regioselective reaction;	95%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-Ethoxyaniline (156-43-4) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-ethoxylphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 14h; regioselective reaction;	95%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 6-methoxy-tetral-4-one thiosemicarbazone (304458-95-5) → 4-cyclopropyl-5-(2-fluorophenyl)-2-((6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazono)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.5h; Reagent/catalyst; Solvent; Temperature; Hantzsch Thiazole Synthesis; Reflux;	95%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-Ethoxyaniline (156-43-4) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-ethoxylphenylimino)-4-cyclopropyl-5-(2'-fluoro-phenyl)-thiazole

Conditions	Yield
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 0.75h; regioselective reaction;	95%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 2-(3,4-dihydronaphthalen-1(2H)-ylidene)hydrazinecarbothioamide (3689-17-6) → 4-cyclopropyl-2-((3,4-dihydronaphthalen-1(2H)-ylidene)hydrazono)-5-(2-fluorophenyl)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.5h; Hantzsch Thiazole Synthesis; Reflux;	94%

4-HYDROXYPIPERIDINE (5382-16-1) + 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) → 1-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4-hydroxypiperidine

Conditions	Yield
With potassium carbonate In N-methyl-acetamide; water	93%
With potassium carbonate In N-methyl-acetamide; water	93%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) → (5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)boronic acid (1263407-24-4)

Conditions	Yield
Stage #1: C7H10BNO2S*C7H8O3S With triethylamine In ethanol at 50℃; Inert atmosphere; Stage #2: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone In ethanol at 50℃; for 8h;	93%

+ 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) → 3-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)thiazolidine-2,4-dione (1563931-94-1)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 6h;	93%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-methoxy-aniline (104-94-9) + methyl thioisocyanate (556-61-6) → 3-methyl-2-(4'-methoxyphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 16h; regioselective reaction;	93%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1.5h; regioselective reaction;	93%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 1-indanone thiosemicarbazone (74227-66-0) → 4-cyclopropyl-2-((2,3-dihydro-1H-inden-1-ylidene)hydrazono)-5-(2-fluorophenyl)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.333333h; Hantzsch Thiazole Synthesis; Reflux;	93%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + Ethyl isothiocyanate (542-85-8) + 4-aminoethylbenzene (589-16-2) → 3-ethyl-2-(4'-ethylphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 14h; regioselective reaction;	92%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1.5h; regioselective reaction;	92%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + Ethyl isothiocyanate (542-85-8) + 4-Ethoxyaniline (156-43-4) → 3-ethyl-2-(4'-ethoxyphenylimino)-4-cyclopropyl-5-(2'-fluoro-phenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 12h; regioselective reaction;	91%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 2h; regioselective reaction;	91%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 1-(1-(4-methoxyphenyl)ethylidene)thiosemicarbazide (16546-08-0) → 4-cyclopropyl-5-(2-fluorophenyl)-2-(2-(1-(4-methoxyphenyl)ethylidene)hydrazinyl)thiazole

Conditions	Yield
With triethylamine In ethanol for 0.583333h; Hantzsch Thiazole Synthesis; Reflux;	91%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 5,6,7,7a-tetrahydrothieno[3,2-c]pyridine-2(4H)-one monohydrochloride (109904-37-2) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (952340-38-4)

Conditions	Yield
Stage #1: 5,6,7,7a-tetrahydrothieno[3,2-c]pyridine-2(4H)-one monohydrochloride With triethylamine In dichloromethane at 10℃; for 0.25h; Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 10℃; Stage #3: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone With triethylamine; sodium iodide In dichloromethane at 10 - 25℃; Temperature;	90%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 1-(1-(3,4-dimethoxyphenyl)ethylidene)thiosemicarbazide (71173-46-1) → 4-cyclopropyl-2-((1-(3,4-dimethoxyphenyl)ethylidene)hydrazono)-5-(2-fluorophenyl)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.666667h; Hantzsch Thiazole Synthesis; Reflux;	90%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-methoxy-aniline (104-94-9) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-methoxyphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 16h; regioselective reaction;	89%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 0.75h; regioselective reaction;	89%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 2-(1-(4-tolyl)ethylidene)hydrazinecarbothioamide (7410-54-0) → 4-cyclopropyl-5-(2-fluorophenyl)-2-((1-(p-tolyl)ethylidene)hydrazono)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.583333h; Hantzsch Thiazole Synthesis; Reflux;	89%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-bromo-aniline (106-40-1) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-bromophenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 20h; regioselective reaction;	88%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1.25h; regioselective reaction;	88%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 2-[1-(4-nitrophenyl)ethylidene]hydrazine-1-carbothioamide (5424-45-3) → 4-cyclopropyl-5-(2-fluorophenyl)-2-((1-(4-nitrophenyl)ethylidene)hydrazono)-2,3-dihydrothiazole

Conditions	Yield
With triethylamine In ethanol for 0.5h; Hantzsch Thiazole Synthesis; Reflux;	88%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + C8H14BrNO2S → C19H23BrFNO3S

Conditions	Yield
With potassium phosphate; iodine at 80℃; for 7h; Temperature; Reagent/catalyst;	87.1%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + m-Anisidine (536-90-3) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(3'-methoxyphenylimino)-4-cyclopropyl-5-(2'-fluoro-phenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 18h; regioselective reaction;	87%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1h; regioselective reaction;	87%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-chloro-aniline (106-47-8) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-chlorophenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 20h; regioselective reaction;	87%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1.25h; regioselective reaction;	87%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 4-amino-phenol (123-30-8) + N-allyl isothiocyanate (57-06-7) → 3-allyl-2-(4'-hydroxyphenylimino)-4-cyclopropyl-5-(2'-fluorophenyl)-thiazole

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 24h; regioselective reaction;	82%
With 1-octyl-3-methylimidazole hexafluorophosphate at 20℃; for 1h; regioselective reaction;	82%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + (E)-4-(acetylsulfanyl)-3-((1-[(2-pyridyl)methyl]-1H-pyrazol-3-yl)methylidene)piperidine bis(hydrogen trifluoroacetate) → (E)-4-(acetylsulfanyl)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-((1-[(2-pyridyl)methyl]-1H-pyrazol-3-yl)methylidene)piperidine

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 0.5h;	81%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + (E)-4-(acetylsulfanyl)-3-((1-[3-(ethoxycarbonyl)propyl]-1H-1,2,3-triazol-4-yl)methylidene)piperidine hydrogen trifluoroacetate (853805-52-4) → (E)-4-(acetylsulfanyl)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-((1-[3-(ethoxycarbonyl)propyl]-1H-1,2,3-triazol-4-yl)methylidene)piperidine

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 2.5h;	77%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + (E)-3-[(furan-2-yl)methylidene]piperidin-4-ol hydrogen acetate → (E)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-[(furan-2-yl)methylidene]piperidin-4-ol

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 1h;	74%

Upstream product

• 150322-73-9 1-cyclopropyl-2-(2-fluorophenyl)ethanone 
• 446-48-0 o-fluorobenzyl bromide 
• 57486-67-6 methyl o-fluorophenylacetate 
• 462-06-6 fluorobenzene 
• 4606-07-9 ethyl cyclopropylcarboxylate 
• 326-62-5 2-fluorophenyl acetonitrile 
• 345-35-7 2-fluorobenzyl chloride 
• 946402-23-9 2-(2-fluorophenyl)-N-methoxy-N-methylacetamide 
• 451-82-1 (2-fluorophenyl)acetic acid 

Downstream Products

• 150322-43-3 prasugel 
• 150322-38-6 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one 
• 1243654-57-0 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine hydrobromide 
• 150322-39-7 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydro thieno[3,2-c] pyridine hydrochloride 
• 1287752-37-7 1-cyclopropyl-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(2-fluorophenyl)ethanone hydrobromide salt 
• 952340-38-4 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 1618107-96-2 5-(5-chloro-1-(2-fluorophenyl)-2-oxopentyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate hydrochloride 
• 1056459-37-0 2-acetoxy-5-[5-chloro-1-(2-fluorophenyl)-2-oxopentyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 

Relevant articles and documents

2 - Bromo 2 - (2 - fluorophenyl) ethanone preparation of cyclopropyl (by machine translation)

The invention belongs to the technical field of medicines and particularly relates to a preparation method of a medicine intermediate, and more particularly relates to a preparation method of a prasugrel intermediate cyclopropyl-2-bromo-2-(2-fluorophenyl) ethanone. The preparation method comprises the following steps: carrying out reaction on 2-fluorophenylacetate and cyclopropane carbonyl chloride to prepare cyclopropyl-2-(2-fluorophenyl) ethanone; and then, carrying out halogenating reaction with a bromination reagent to prepare cyclopropyl-2-bromo-2-(2-fluorophenyl) ethanone. The preparation method provided by the invention is carried out under a relatively mild condition, raw materials are easily available, and the obtained product is high in purity and relatively high in yield which reaches over 70%, so that the preparation method is suitable for industrial production.

An anti-platelet drug prasugrel method for the preparation of (by machine translation)

The invention discloses an anti-platelet drug prasugrel method for preparing, the method includes: 1) the 1 [...] cyclopropyl -2 the [...] (the 2 [...] phenyl) - 2 the and iodine monobromide[...] ethanone and the 1 [...] butyl -3 the imidazolium methyl bromination[...] contact is obtained by reacting the 1 [...] cyclopropyl -2 the- [...] the 2 [...] (the 2 [...] phenyl) - 2 the [...] ethanone; 2) and in iodine under the presence of alkali, the step 1) product with the 2 [...] oxo -2, 4, 5, 6, 7 the [...] the 7a [...] tetrahydro-thieno [3,2 the ??c] pyridine hydrochloride is obtained by reacting the 5 [...] (α-cyclopropane carbonyl -2 the [...] fluorobenzyl) - 2 the [...] oxo -2, 4, 5, 6, 7, 7a-tetrahydro-thieno [3,2 the ??c] pyridine; 3) steps 2) product with triethylamine mixed, then instillment second grade anhydride, shall prasugrel stirring reaction. The method of preparing the prasugrel of this invention high yield, is easy to be treated, is suitable for industrial production. (by machine translation)

IMPROVED PROCESS FOR THE PREPARATION OF PRASUGREL AND INTERMEDIATE THEREOF

The invention relates to an industrial scale process for the preparation of l-cyclopropyl-2-(2- fluorophenyl)-ethanone of the Formula (1) and the use of this compound for the preparation of prasugrel.