1973-22-4

Basic information

• Product Name: 2-Bromoethylbenzene
• Synonyms: 2-ETHYLBROMOBENZENE;1-BROMO-2-ETHYLBENZENE;O-BROMOETHYLBENZENE;1-Ethyl-2-brombenzol;1-Ethyl-2-bromobenzene;2-Bromo-1-ethylbenzene;benzene,1-bromo-2-ethyl-;o-ethylbromobenzene
• CAS NO: 1973-22-4
• Molecular Formula: C₈H₉Br
• Molecular Weight: 185.06
• EINECS: 217-823-8
• Product Categories: Benzene derivates;Bromine Compounds;Aryl;C8;Halogenated Hydrocarbons;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 1973-22-4.mol
• Article Data: 26

Chemical Properties

• Melting Point: -56 °C
• Boiling Point: 199 °C(lit.)
• Flash Point: 171 °F
• Appearance: Clear colourless to light yellow liquid
• Density: 1.338 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.471mmHg at 25°C
• Refractive Index: n20/D 1.549(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1929735
• CAS DataBase Reference: 2-Bromoethylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromoethylbenzene(1973-22-4)
• EPA Substance Registry System: 2-Bromoethylbenzene(1973-22-4)

Safety Data

• Hazard Codes: Xi,N,O
• Statements: 36/37/38-51/53
• Safety Statements: 26-61-24/25
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 3
• F: 9
• HazardClass: IRRITANT
• Hazardous Substances Data: 1973-22-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear colourless to light yellow liquid

Uses

1-Bromo-2-ethylbenzene may be used in the synthesis of:1-(2′-ethylphenyl)ethanolN-benzyl-P-(2-ethylphenyl)-P-phenylphosphinic amide4-(isopropyldimethylsilyl)-2-(2-ethylphenyl)pyridine5-amino-2′-ethyl -biphenyl-2-ol, used for modification of carbon paste electrode

General Description

1-Bromo-2-ethylbenzene is an organobromine compound.

InChI:InChI=1/C8H9Br/c1-2-7-5-3-4-6-8(7)9/h3-6H,2H2,1H3

Synthetic route

2-bromostyrene (2039-88-5) → 1-bromo-2-ethylbenzene (1973-22-4)

Conditions	Yield
With methanol; palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Schlenk technique; Inert atmosphere;	99%
With methanol; palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;	70%
With hydrogen In ethanol at 80℃; under 15001.5 Torr; Flow reactor; Green chemistry; chemoselective reaction;	18%
With platinum; benzene Hydrogenation;
With sodium acetate trihydrate; toluene-4-sulfonic acid hydrazide In tetrahydrofuran at 80℃; for 12h; Inert atmosphere;

ethylbenzene (100-41-4) → 1-bromo-4-ethylbenzene (1585-07-5) + 1-bromo-2-ethylbenzene (1973-22-4)

Conditions	Yield
With oxygen; sodium bromide In dibutyl ether at 45℃; under 760.051 Torr; for 5h; Schlenk technique;	A 83% B 9%
With carbon dioxide; bromine at 40℃; under 187519 Torr; for 2h; Supercritical conditions; Green chemistry;	A 64% B 36%
With ammonium nitrate; N-Bromosuccinimide In acetonitrile for 8h;	A 53% B 30%

ethyl bromide (74-96-4) + bromobenzene (108-86-1) → 1-bromo-4-ethylbenzene (1585-07-5) + 1-bromo-2-ethylbenzene (1973-22-4)

Conditions	Yield
With aluminium at 80℃;

ortho-ethylaniline (578-54-1) → 1-bromo-2-ethylbenzene (1973-22-4)

Conditions	Yield
With hydrogen bromide; copper(I) bromide; sodium nitrite
With hydrogen bromide; copper; sodium nitrite
(i) aq. HBr, NaNO2, (ii) Cu; Multistep reaction;
(i) NaNO2, aq. HBr, (ii) Cu; Multistep reaction;
(i) (diazotization), aq. HBr, (ii) Cu; Multistep reaction;

bromobenzene (108-86-1) + ethene (74-85-1) → 1-bromo-4-ethylbenzene (1585-07-5) + 1-bromo-2-ethylbenzene (1973-22-4) + 1-bromo-3-ethylbenzene (2725-82-8)

Conditions	Yield
H-ZSM-5 catalyst at 400℃; Product distribution; alkylation of benzene and momosubstituted benzenes with ethylene over H-ZSM-5 and mordenite-H catalysts; isomerization of ethylarenes over H-mordenite;

1-bromo-4-ethylbenzene (1585-07-5) → 1-bromo-2-ethylbenzene (1973-22-4) + 1-bromo-3-ethylbenzene (2725-82-8)

Conditions	Yield
H-mordenite at 250℃; Product distribution; alkylation of benzene and momosubstituted benzenes with ethylene over H-ZSM-5 and mordenite-H catalysts; isomerization of ethylarenes over H-mordenite;

ethylbenzene (100-41-4) → bromobenzene (108-86-1) + 1-bromo-4-ethylbenzene (1585-07-5) + 1-bromo-2-ethylbenzene (1973-22-4)

Conditions	Yield
With hydrogen bromide; dihydrogen peroxide at 50℃; Product distribution; Kinetics; Thermodynamic data; oth. temperature, var. stirring rate, var. ratio of reactants, E(activ.), ΔH(activ.), ΔS(activ.), ΔG(activ.);	A 1.6 % Chromat. B 73.3 % Chromat. C 22.2 % Chromat.
With hydrogenchloride; sodium hypochlorite; sodium bromide In water at 19.85℃; for 5h; Product distribution; Further Variations:; Temperatures;

ethylbenzene (100-41-4) → 1-bromo-4-ethylbenzene (1585-07-5) + 1-bromo-2-ethylbenzene (1973-22-4) + 1-bromo-3-ethylbenzene (2725-82-8)

Conditions	Yield
With bromine; iron(III) chloride In acetic acid at 25 - 75℃; Rate constant; Product distribution; other solvents (nitromethane, acetic anhydride), k (rel. to benzene);

1-bromo-2-(2-iodoethyl)benzene (113163-19-2) → 1-bromo-2-(2-bromoethyl)benzene (1074-15-3) + ethylbenzene (100-41-4) + 1-bromo-2-ethylbenzene (1973-22-4) + 2-phenethyl iodide (17376-04-4) + 2-bromostyrene (2039-88-5) + 1-phenyl-2-bromoethane (103-63-9)

Conditions	Yield
With methanol; tert.-butyl lithium In tetrahydrofuran at -98℃; Product distribution; Mechanism;

(4-Bromo-3-ethyl-phenyl)-trimethyl-silane → 1-bromo-2-ethylbenzene (1973-22-4)

Conditions	Yield
With potassium fluoride In N,N-dimethyl-formamide at 50℃; for 3h; Yield given;

biphenyl (92-52-4) + 1-ethyl-2-bromo-4-tert-butyl-benzene (57190-08-6) → 1-bromo-2-ethylbenzene (1973-22-4)

Conditions	Yield
With aluminium trichloride In tetrachloromethane; nitromethane

ethyl bromide (74-96-4) + bromobenzene (108-86-1) + aluminium → 1-bromo-4-ethylbenzene (1585-07-5) + 1-bromo-2-ethylbenzene (1973-22-4)

ethylbenzene (100-41-4) + bromine (7726-95-6) → 1-bromo-4-ethylbenzene (1585-07-5) + 1-bromo-2-ethylbenzene (1973-22-4)

ethylbenzene (100-41-4) + bromine (7726-95-6) + iodine (7553-56-2) → 1-bromo-4-ethylbenzene (1585-07-5) + 1-bromo-2-ethylbenzene (1973-22-4)

2-Ethyl-1,4-bis-trimethylsilanyl-benzene (128254-32-0) → 1-bromo-2-ethylbenzene (1973-22-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: Br2 2: KF / dimethylformamide / 3 h / 50 °C View Scheme

4-ethyl-tert-butylbenzene (7364-19-4) → 1-bromo-2-ethylbenzene (1973-22-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: Fe, Br2 / CCl4 2: AlCl3 / CCl4; nitromethane View Scheme

ortho-bromobenzaldehyde (6630-33-7) → 1-bromo-2-ethylbenzene (1973-22-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 - 25 °C / Inert atmosphere 2: toluene-4-sulfonic acid hydrazide; sodium acetate trihydrate / tetrahydrofuran / 12 h / 80 °C / Inert atmosphere View Scheme

2-bromostyrene (2039-88-5) + hydrogen (1333-74-0) → 1-bromo-2-ethylbenzene (1973-22-4)

Conditions	Yield
With [Ir(6-Neo)(COD)Cl] In ethanol under 3750.38 Torr; for 1h;	69 %Spectr.

carbon monoxide (201230-82-2) + 2-bromostyrene (2039-88-5) → 1-bromo-2-ethylbenzene (1973-22-4) + C9H9BrO + C9H9BrO + 3-(o-bromophenyl)propanal (107408-16-2)

Conditions	Yield
With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride In toluene at 40℃; under 30003 Torr; for 128h; Autoclave; Schlenk technique; enantioselective reaction;	A n/a B n/a C n/a D n/a
With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride In toluene at 100℃; under 30003 Torr; for 24h; Temperature; Autoclave; Schlenk technique; enantioselective reaction;	A n/a B n/a C n/a D n/a

1-bromo-2-ethylbenzene (1973-22-4) + 2,4,6-trimethylaniline (88-05-1) → 2,4,6-trimethylphenyl-2'-ethyldiphenylamine

Conditions	Yield
With palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate In toluene at 100℃; for 12h;	99%
With bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate; palladium dichloride In toluene at 80℃; for 18h;	97%
With palladium diacetate; sodium t-butanolate; tri-t-butylphosphonium tetraphenylborate complex In toluene at 110℃; for 3h; Inert atmosphere;	30 g
With palladium diacetate; sodium t-butanolate; tri-t-butylphosphonium tetraphenylborate complex In toluene at 110℃; for 3h; Inert atmosphere;	30 g

1-bromo-2-ethylbenzene (1973-22-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-ethylbenzaldehyde (22927-13-5)

Conditions	Yield
Stage #1: 1-bromo-2-ethylbenzene In dichloromethane; cyclohexane at -78 - -75℃; for 1.5h; Stage #2: N,N-dimethyl-formamide In dichloromethane; cyclohexane for 1h; Solvent;	99%
Stage #1: 1-bromo-2-ethylbenzene With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 3h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexanes at -78℃; for 3h;	96%
Stage #1: 1-bromo-2-ethylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 0.5h;	85%
Stage #1: 1-bromo-2-ethylbenzene With n-butyllithium Stage #2: N,N-dimethyl-formamide Further stages.;
Stage #1: 1-bromo-2-ethylbenzene With magnesium In tetrahydrofuran for 2h; Heating / reflux; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 0.5h; Stage #3: With hydrogenchloride; water In tetrahydrofuran

1-bromo-2-ethylbenzene (1973-22-4) → 2-bromophenyl methyl ketone (2142-69-0)

Conditions	Yield
With Iron(III) nitrate nonahydrate; 1-hydroxy-pyrrolidine-2,5-dione; oxygen In benzonitrile at 90℃; for 21h;	99%
With Iron(III) nitrate nonahydrate; N-hydroxyphthalimide In benzonitrile at 100℃; for 20h;	95%
With tert.-butylhydroperoxide In acetonitrile at 25 - 35℃; for 20h; Sealed tube; Irradiation;	75%

1-bromo-2-ethylbenzene (1973-22-4) + 1-(tert-butoxycarbonyl)-4-aminopiperidine (87120-72-7) → 1-tert-butoxycarbonyl-4-[(2-ethylphenyl)amino]piperidine (933056-02-1)

Conditions	Yield
With sodium t-butanolate; DavePhos; tris-(dibenzylideneacetone)dipalladium(0) In xylene at 130℃; for 24h;	98%

1-bromo-2-ethylbenzene (1973-22-4) → 1-(2-bromophenyl)ethanol (5411-56-3)

Conditions	Yield
With wild type cytochrome P450 CYP102A1(P450Bm3); oxygen; NADPH Reagent/catalyst; Enzymatic reaction;	98%
With Mn(II)T(p-Cl)PP; oxygen In neat (no solvent) at 140℃; under 13501.4 Torr; for 6h; Sealed tube;	10.5%
Multi-step reaction with 2 steps 1: sodium anthraquinonesulfonate; air / water; acetonitrile / 18 h / 20 °C / Irradiation 2: sodium tetrahydroborate; methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: dihydroxy-methyl-borane; lithium carbonate; N-fluorobis(benzenesulfon)imide; bathophenanthroline; copper (I) acetate / chlorobenzene / 16 h / 55 °C / Glovebox; Inert atmosphere 2: 1,1,1,3',3',3'-hexafluoro-propanol; water / chlorobenzene; dichloromethane / 16 h / 20 °C / Sealed tube View Scheme

n-butyllithium (109-72-8, 29786-93-4) + 1-bromo-2-ethylbenzene (1973-22-4) → 2-(n-butyl)ethylbenzene (42548-38-9)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); water; sodium chloride In cyclohexane at 20℃; for 0.00555556h; pH=6; Schlenk technique;	98%

1-bromo-2-ethylbenzene (1973-22-4) + sec.-butyllithium (598-30-1) → 1-sec-butyl-2-ethylbenzene

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); water; sodium chloride In cyclohexane at 20℃; for 0.00555556h; pH=6; Schlenk technique;	98%

1-bromo-2-ethylbenzene (1973-22-4) + phenyllithium (591-51-5) → 2-ethyl-1,1'-biphenyl (1812-51-7)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); water; sodium chloride In dibutyl ether at 20℃; for 0.00555556h; pH=6; Schlenk technique;	98%

1-bromo-2-ethylbenzene (1973-22-4) → (beta-bromoethyl)monobromobenzene (62384-31-0)

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 3h; Heating / reflux;	97%
With carbon tetrabromide; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In dichloromethane at 20℃; for 36h; Schlenk technique; Inert atmosphere; Irradiation;
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Inert atmosphere; Reflux;

diethylchlorophosphine (686-69-1) + 1-bromo-2-ethylbenzene (1973-22-4) → diethyl(o-ethylphenyl)phosphane (1085850-79-8)

Conditions	Yield
Stage #1: 1-bromo-2-ethylbenzene With n-butyllithium In diethyl ether at -10 - 0℃; for 3h; Stage #2: diethylchlorophosphine In diethyl ether at 20℃; Further stages.;	97%

1-bromo-2-ethylbenzene (1973-22-4) + N-(4-chlorobenzylidene)-N-(1,1,1-trimethylsilyl)amine (85654-07-5) → (4-chlorobenzylidene)(2-ethylphenyl)amine

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 90℃; for 14h;	96%

1-bromo-2-ethylbenzene (1973-22-4) + phenylboronic acid (98-80-6) → 2-ethyl-1,1'-biphenyl (1812-51-7)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere;	96%
With C25H29FeI2N3OPd; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 19h; Suzuki-Miyaura Coupling; Schlenk technique; Sealed tube;
With potassium carbonate In ethanol; water at 70℃; for 0.75h; Suzuki Coupling;	72 %Chromat.
With C36H36Cl2Fe2NPPd; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 18h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	57 %Chromat.

1-bromo-2-ethylbenzene (1973-22-4) + N-trimethylsilyl(4-methoxy)benzaldimine (64187-51-5) → (2-ethylphenyl)(4-methoxybenzylidene)amine

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 90℃; for 14h;	95%

styrene (292638-84-7) + 1-bromo-2-ethylbenzene (1973-22-4) → 1-ethyl-2-styrylbenzene

Conditions	Yield
With N-[2-(pyrazol-1-yl)phenyl]-N'-benzylimidazol-2-ylidene palladium chloride; potassium carbonate In water; N,N-dimethyl-formamide Reagent/catalyst; Heck Reaction;	95%
With dichlorobis(tri-O-tolylphosphine)palladium; N-Methyldicyclohexylamine; 4,4'-di-tert-butylbiphenyl; tetrabutyl-ammonium chloride In N,N-dimethyl acetamide at 80℃; for 24h; Reagent/catalyst; Heck Reaction; Glovebox;
With N,N-dimethyl-cyclohexanamine; tetrabutyl-ammonium chloride; palladium diacetate; triphenylphosphine In N,N-dimethyl acetamide at 80℃; for 24h; Heck Reaction;	18 %Spectr.

1-bromo-2-ethylbenzene (1973-22-4) + copper(l) cyanide → o-ethylbenzonitrile (34136-59-9)

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; for 12h;	95%

1-bromo-2-ethylbenzene (1973-22-4) + 2,3-dihydro-2-methyl-1H-inden-1-one (17496-14-9) → (S)-2-(2-ethylphenyl)-2-methyl-2,3-dihydro-1H-inden-1-one

Conditions	Yield
With (R)-BIDIME; palladium diacetate; sodium t-butanolate In toluene at 80℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere; enantioselective reaction;	95%

1-bromo-2-ethylbenzene (1973-22-4) + propionaldehyde (123-38-6) → 1-(2-ethylphenyl)propanol (67541-89-3)

Conditions	Yield
Stage #1: 1-bromo-2-ethylbenzene With iodine; magnesium In tetrahydrofuran at -5 - 5℃; for 2h; Stage #2: propionaldehyde In tetrahydrofuran at 20℃;	95%

1-bromo-2-ethylbenzene (1973-22-4) + 2-{[allyl(benzyl)amino]methyl}-N-(4-methoxyphenyl)aniline (1284151-57-0) → 4-benzyl-2-(2-ethylbenzyl)-1-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine (1284151-70-7)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); cyclohexyldiphenylphosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 135℃; Inert atmosphere;	94%

isopropylboronic acid (80041-89-0) + 1-bromo-2-ethylbenzene (1973-22-4) → 1-ethyl-2-isopropylbenzene (18970-44-0)

Conditions	Yield
With potassium phosphate monohydrate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; C20H34O3P2 In toluene at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	94%

1-bromo-2-ethylbenzene (1973-22-4) + n-hexyllithium (21369-64-2) → 1-ethyl-2-hexylbenzene (71521-85-2)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); water; sodium chloride In hexane at 20℃; for 0.00555556h; pH=6; Schlenk technique;	94%

1-bromo-2-ethylbenzene (1973-22-4) + N-(2-furylmethylidene)-N-(1,1,1-trimethylsilyl)amine (83948-29-2) → (2-ethylphenyl)(furan-2-ylmethylene)amine

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 90℃; for 14h;	92%

1-bromo-2-ethylbenzene (1973-22-4) + methyl thioisocyanate (556-61-6) → 2-ethyl-N-methylthiobenzamide (489470-19-1)

Conditions	Yield
Stage #1: 1-bromo-2-ethylbenzene With magnesium In tetrahydrofuran Stage #2: methyl thioisocyanate In tetrahydrofuran at 20℃; for 16h;	91%

1-bromo-2-ethylbenzene (1973-22-4) + N-(2,4,6-trimethylphenyl)-1,2-diaminoethane (444325-38-6) → N1-(2-ethylphenyl)-N2-mesitylethane-1,2-diamine

Conditions	Yield
With (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In 1,2-dimethoxyethane at 80℃; for 17h; Glovebox; Inert atmosphere; Sealed tube;	91%

1-bromo-2-ethylbenzene (1973-22-4) + DL-3-aminohexahydro-1H-azepin (69154-03-6) → 3-[(2-ethylphenyl)amino]hexahydroazepine

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In xylene at 130℃; for 24h;	90%

1-bromo-2-ethylbenzene (1973-22-4) + 1,1-diphenyl-2-methyl-2-propen-1-ol (29291-01-8) → 2-(2-ethylphenyl)methyl-2-methyl-3,3-diphenyloxirane (1116366-33-6)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); sodium t-butanolate; ruphos In toluene for 6h; Inert atmosphere; Reflux;	90%

1-bromo-2-ethylbenzene (1973-22-4) + Methyl cinnamate (103-26-4) → Methyl (Z)-3-(2-ethylphenyl)-3-phenylacrylate + Methyl (E)-3-(2-ethylphenyl)-3-phenylacrylate

Conditions	Yield
With N-Methyldicyclohexylamine; tetraethylammonium chloride; palladium diacetate In N,N-dimethyl acetamide at 85℃; for 60h; Arylation; Heck arylation;	A n/a B 89%

1-bromo-2-ethylbenzene (1973-22-4) + (1R,4S,6S)-bicyclo<2.2.2>octane-6-ol-2-one (129100-39-6) → (1R,2R,4S,6S)-2-(2-ethylphenyl)bicyclo[2.2.2]octane-2,6-diol (1067234-14-3)

Conditions	Yield
Stage #1: 1-bromo-2-ethylbenzene In tetrahydrofuran Stage #2: (1R,4S,6S)-bicyclo<2.2.2>octane-6-ol-2-one In tetrahydrofuran; diethyl ether at 25℃; for 1h; Grignard reaction; Further stages.;	89%

1-bromo-2-ethylbenzene (1973-22-4) + diphenyldisulfane (882-33-7) → 2-ethylphenyl phenyl sulfide (23075-79-8)

Conditions	Yield
With C40H32N4O7Ti2(2+)*2C8F17O3S(1-); zinc In toluene at 35℃; for 10h;	89%

1-bromo-2-ethylbenzene (1973-22-4) + (E)-tert-butyl 3-(4-((6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (1622308-34-2) → (E)-tert-butyl 3-(4-((2-(2-ethylphenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (1622308-65-9)

Conditions	Yield
With chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 150℃; for 2h; Microwave irradiation; Sealed tube; Inert atmosphere;	89%

Upstream product

• 74-96-4 ethyl bromide 
• 108-86-1 bromobenzene 
• 100-41-4 ethylbenzene 
• 74-85-1 ethene 
• 7726-95-6 bromine 
• 7553-56-2 iodine 
• 7364-19-4 4-ethyl-tert-butylbenzene 
• 201230-82-2 carbon monoxide 
• 2039-88-5 2-bromostyrene 
• 1333-74-0 hydrogen 
• 6630-33-7 ortho-bromobenzaldehyde 
• 128254-32-0 2-Ethyl-1,4-bis-trimethylsilanyl-benzene 
• 92-52-4 biphenyl 
• 57190-08-6 1-ethyl-2-bromo-4-tert-butyl-benzene 

Downstream Products

• 1585-07-5 1-bromo-4-ethylbenzene 
• 2725-82-8 1-bromo-3-ethylbenzene 
• 100-41-4 ethylbenzene 
• 5530-23-4 2-Ethyl-1-(2-ethyl-phenyl)-cyclohexan-1-ol 
• 5530-24-5 2-Isopropyl-1-(2-ethyl-phenyl)-cyclohexan-1-ol 
• 4973-03-9 1-(2-Ethyl-phenyl)-2-methyl-cyclohexanol 
• 183722-07-8 Di-adamantan-1-yl-(2-ethyl-phenyl)-methanol 
• 180745-06-6 2-Ethyl-dithiobenzoic acid methyl ester 
• 88-65-3 2-bromobenzoic-acid 
• 22927-13-5 2-ethylbenzaldehyde 
• 2142-69-0 2-bromophenyl methyl ketone 
• 29778-18-5 1-ethyl-2-(phenylethynyl)benzene 
• 56427-44-2 ethyl ester of ortho-ethylbenzoic acid 
• 2029-73-4 2-ethyl-benzhydrol 

Relevant articles and documents

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Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration

A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).

On the ionizing properties of supercritical carbon dioxide: Uncatalyzed electrophilic bromination of aromatics

Supercritical carbon dioxide (scCO2), a solvent with a zero dipole moment, low dielectric constant, and no hydrogen bonding behavior, is a suitable medium to perform the uncatalyzed electrophilic bromination of weakly activated aromatics with no interference of radical pathways. The ability of scCO2 to promote these reactions matches those of strongly ionizing solvents such as aqueous acetic and trifluoroacetic acids. Conversely, carbon tetrachloride, with similar polarity parameters to scCO2, leads exclusively to side chain functionalization. The strong quadrupole moment, and the acidic, but non basic, Lewis character of carbon dioxide, are proposed as key factors for the singular performance of scCO2 in reactions involving highly polar and ionic intermediates.