2398-37-0

Basic information

• Product Name: 3-Bromoanisole
• Synonyms: M-BROMOANISOLE;META BROMO ANISOLE;BROMOANISOLE(3-);1-BROMO-3-METHOXYBENZENE;5-bromoanisole;3-BROMO ANISOL;3-BROMOANISOLE;TIMTEC-BB SBB007886
• CAS NO: 2398-37-0
• Molecular Formula: C₇H₇BrO
• Molecular Weight: 187.03
• EINECS: 219-264-5
• Product Categories: Aromatics Compounds;Tramadol;Aromatics;alkyl bromide;3-Bromoanisole ada@tuskwei.com whatsapp;8618031153937
• Mol File: 2398-37-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 2 °C
• Boiling Point: 210-211 °C(lit.)
• Flash Point: 200 °F
• Appearance: Clear colorless to slightly yellow-brown/Liquid
• Density: 1.490 g/mL at 20 °C
• Vapor Pressure: 0.278mmHg at 25°C
• Refractive Index: n20/D 1.563(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• Water Solubility: Miscible in methanol, benzene, hexane, toluene and dichloromethane. Practically insoluble in water.
• Stability: Stable. Combustible. Incompatible with strong oxidising agents, strong acids reducing agents.
• BRN: 1524687
• CAS DataBase Reference: 3-Bromoanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromoanisole(2398-37-0)
• EPA Substance Registry System: 3-Bromoanisole(2398-37-0)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 8
• TSCA: T
• Hazardous Substances Data: 2398-37-0(Hazardous Substances Data)

Usage

Chemical Properties

Colorless Clear Liquid

Uses

3-Bromoanisole used in chemical reaction as intermediates to obtain target materials such as dyes, pharmaceuticals, perfumes, photoinitiators and agrochemicals.

InChI:InChI=1/C7H7BrO/c1-9-7-4-2-3-6(8)5-7/h2-5H,1H3

Synthetic route

3-Bromophenol (591-20-8) + methyl iodide (74-88-4) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 16h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	92%

3-Bromophenol (591-20-8) + dimethyl sulfate (77-78-1) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
Stage #1: 3-Bromophenol With potassium carbonate In acetone for 0.25h; Stage #2: dimethyl sulfate In acetone for 10h; Reflux;	95%
With sodium hydroxide
With sodium hydroxide

3-Bromophenol (591-20-8) + carbonic acid dimethyl ester (616-38-6) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In sulfolane at 220℃; for 0.166667h;	95%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 220℃; for 0.166667h; Inert atmosphere;	94%

methanol (67-56-1) + 3-Bromonitrobenzene (585-79-5) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
Stage #1: methanol With tetrabutyl-ammonium chloride; potassium hydroxide In cyclohexane at 55℃; for 0.0833333h; Stage #2: m-nitrobromobenzene In cyclohexane at 55 - 60℃; for 3h; Reagent/catalyst;	83%

3-Bromonitrobenzene (585-79-5) + sodium methylate (124-41-4) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In n-heptane at 20 - 50℃; for 3h; Reagent/catalyst;	82%

3-methoxybenzenediazonium o-benzenedisulfonimide → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution;	78%
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution;	72%

methanol (67-56-1) + 3-bromophenyl(mesityl)iodonium bromide → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
Stage #1: methanol With sodium hydride In tert-butyl methyl ether; mineral oil at 20℃; for 0.25h; Inert atmosphere; Sealed tube; Stage #2: 3-bromophenyl(mesityl)iodonium bromide In tert-butyl methyl ether; mineral oil at 50℃; for 1h; Inert atmosphere; Sealed tube; chemoselective reaction;	77%

(2,4,6-trimethylphenyl)(3’-methoxyphenyl)iodonium triflate (1464149-60-7) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
With copper(I) bromide In acetonitrile at 80℃; for 2h;	64%

m-Anisidine (536-90-3) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
Stage #1: m-Anisidine With Bromotrichloromethane; sodium nitrite In dichloromethane; water at 23℃; for 0.0833333h; Stage #2: With acetic acid In dichloromethane; water at 23℃; for 24h; Temperature;	28%
With sulfuric acid; sodium nitrite anschliessend Erwaermen mit Kupfer(I)-bromid;
With hydrogen bromide; sodium nitrite anschliessend Erwaermen mit Kupfer-Pulver;

methanol (67-56-1) + m-bromobenzene diazonium nitrate → bromobenzene (108-86-1) + 3-methoxyphenyl bromide (2398-37-0)

methanol (67-56-1) + 3-bromo-benzenediazonium; sulfate → bromobenzene (108-86-1) + 3-methoxyphenyl bromide (2398-37-0)

3-Bromophenol (591-20-8) + methyl p-toluene sulfonate (80-48-8) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
With potassium hydroxide

dimethyl sulfate (77-78-1) + alkaline m-bromo-phenol → 3-methoxyphenyl bromide (2398-37-0)

3-methoxyphenyl(phenyl)iodonium tetrafluoroborate → bromobenzene (108-86-1) + iodobenzene (591-50-4) + 3-methoxyphenyl bromide (2398-37-0) + 3-methoxy-1-iodobenzene (766-85-8)

Conditions	Yield
With BrNBu4 In chloroform at 55℃;

3-bromoaniline (591-19-5) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous H2SO4 / Diazotization.Kochen der Diazoniumsalz-Loesung 2: aqueous NaOH View Scheme
Multi-step reaction with 2 steps 1: aqueous H2SO4 / Diazotization.Kochen der Diazoniumsalz-Loesung 2: aqueous KOH View Scheme

2-bromoanisole (578-57-4) → 3-methoxyphenyl bromide (2398-37-0) + 3-Bromophenol (591-20-8)

(3-methoxyphenyl)(triphenyl-λ5-phosphanyl)gold (870485-34-0) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
With N-Bromosuccinimide In chloroform-d1 at 20℃; chemoselective reaction;	> 95 %Spectr.

3-methoxy-1-iodobenzene (766-85-8) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid 2: copper(I) bromide / acetonitrile / 2 h / 80 °C View Scheme

(3-bromophenyl)boronic acid (89598-96-9) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C 2.1: sodium hydride / tert-butyl methyl ether; mineral oil / 0.25 h / 20 °C / Inert atmosphere; Sealed tube 2.2: 1 h / 50 °C / Inert atmosphere; Sealed tube View Scheme

3-bromo-4-iodoanisole (466639-53-2) → 3-methoxyphenyl bromide (2398-37-0)

Conditions	Yield
With nickel(II) iodide; 1,4-bis(dicyclohexylphosphino)butane; sodium carbonate; cesium iodide In tetrahydrofuran at 35℃; for 72h; Irradiation;

benzophenone (119-61-9) + 3-methoxyphenyl bromide (2398-37-0) → (3-methoxyphenyl)(diphenyl)methanol (78238-98-9)

Conditions	Yield
Stage #1: 3-methoxyphenyl bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	100%
With magnesium 1.) ether, 2.) a) RT, 6 h, b) reflux, 1 h; Yield given. Multistep reaction;
With n-butyllithium

3-methoxyphenyl bromide (2398-37-0) → methoxybenzene (100-66-3)

Conditions	Yield
With tetraphenyldisilane; cesium fluoride In acetonitrile at 100℃; for 0.0833333h;	100%
With tetrakis(triphenylphosphine) palladium(0); formaldehyd; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h;	85%
With N,N,N,N,-tetramethylethylenediamine; C39H46IrN4 In acetonitrile at 45℃; for 48h; Sealed tube; Glovebox; Inert atmosphere;	80%

3-methoxyphenyl bromide (2398-37-0) + 3-methoxy-benzaldehyde (591-31-1) → bis(3-methoxyphenyl)methanol (55360-45-7)

Conditions	Yield
With n-butyllithium In hexane; ethyl acetate	100%
With magnesium In diethyl ether for 1h; Ambient temperature;	62%
With magnesium 1.) ether, ultrasound; Yield given. Multistep reaction;
Stage #1: 3-methoxyphenyl bromide With magnesium In tetrahydrofuran at 0℃; Reflux; Inert atmosphere; Stage #2: 3-methoxy-benzaldehyde In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran
Stage #1: 3-methoxyphenyl bromide With magnesium In diethyl ether at 20℃; for 2h; Inert atmosphere; Stage #2: 3-methoxy-benzaldehyde In diethyl ether at 20℃; for 2h; Inert atmosphere;

3-methoxyphenyl bromide (2398-37-0) + Dichlorophenylphosphine (644-97-3) → bis(3-methoxyphenyl)(phenyl)phosphine oxide (216164-54-4)

Conditions	Yield
Stage #1: 3-methoxyphenyl bromide With magnesium Metallation; Stage #2: Dichlorophenylphosphine Arylation; Stage #3: With water; dihydrogen peroxide In tetrahydrofuran Oxidation; Further stages.;	100%
With magnesium Yield given;

3-methoxyphenyl bromide (2398-37-0) + phenylboronic acid (98-80-6) → 3-methoxybiphenyl (2113-56-6)

Conditions	Yield
With potassium phosphate; 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride; bis(η3-allyl-μ-chloropalladium(II)) In 1,4-dioxane at 80℃; for 12h; Suzuki cross-coupling;	100%
With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene	100%
With potassium phosphate; naphthidine di(radical cation)s-stabilized Pd nanoparticles In 1,4-dioxane at 80℃; for 5h; Suzuki-Miyaura cross-coupling reaction;	99%

3-methoxyphenyl bromide (2398-37-0) + acrylic acid n-butyl ester (141-32-2) → (E)-n-butyl 3-(3-methoxyphenyl)acrylate (346586-17-2)

Conditions	Yield
With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride In N,N-dimethyl acetamide at 140℃; for 12h; Heck reaction;	100%
With di-tert-butylneopentylphosphonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 24℃; for 24h; Heck Reaction; Glovebox;	98%
With bis(1,1'-ethylene-3,3'-divinylimidazole-2,2'-diylidene)nickel(II) dibromide dihydrate; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Heck Reaction; Inert atmosphere; Schlenk technique;	96%

3-methoxyphenyl bromide (2398-37-0) + 1,3-diphenylisobenzofuran (5471-63-6) → 1-methoxy-9,10-diphenyl-9,10-dihydro-9,10-epoxyanthracene

Conditions	Yield
With Me2Zn(TMP)Li In tetrahydrofuran at 20℃; for 12h;	100%
With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex In tetrahydrofuran at -78 - 20℃; for 8h; Inert atmosphere;	84%

3-methoxyphenyl bromide (2398-37-0) + 2-tert-Butylphenol (88-18-6) → 3-tert-butyl-3'-methoxybiphenyl-2-ol

Conditions	Yield
With caesium carbonate; diisopropyl(2-tert-butyl)phenoxyphosphine; RhCl(PPh3)3 In toluene for 18h; Heating;	100%

3-methoxyphenyl bromide (2398-37-0) + m-Anisidine (536-90-3) → 3-methoxy-N-(3-methoxyphenyl)benzenamine (92248-06-1)

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 48h; Buchwald-Hartwig amination;	100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium t-butanolate In toluene at 100℃; for 18h; Buchwald-Hartwig Coupling; Inert atmosphere;	72%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 120℃;	40%
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 72h; Reflux; Inert atmosphere;

3-methoxyphenyl bromide (2398-37-0) + 1-(3-Bromophenyl)ethanone (2142-63-4) → 1-(3-bromo-phenyl)-1-(3-methoxy-phenyl)-ethanol (1180015-29-5)

Conditions	Yield
Stage #1: 3-methoxyphenyl bromide With bromine; magnesium In diethyl ether at 20℃; Stage #2: 1-(3-Bromophenyl)ethanone In diethyl ether for 3h; Reflux;	100%

3-methoxyphenyl bromide (2398-37-0) + 4-methyl-3-(triisopropylsilyloxy)aniline (582322-76-7) → N-(3-methoxyphenyl)-4-methyl-3-(triisopropylsilyloxy)aniline (1643447-98-6)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate In toluene at 100℃; for 31h; Buchwald-Hartwig Coupling; Inert atmosphere;	100%

3-methoxyphenyl bromide (2398-37-0) + Methyl 4-amino-2-methoxybenzoate (27492-84-8) → methyl 2-Methoxy-4-[(3-methoxyphenyl)amino]benzoate (1644060-68-3)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate In toluene at 100℃; for 21h; Inert atmosphere;	100%

3-methoxyphenyl bromide (2398-37-0) + 1-amino-3-methylbenzene (108-44-1) → 3-methoxy-N-(3-methylphenyl)aniline (1449248-83-2)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate In toluene at 100℃; for 15h; Buchwald-Hartwig Coupling; Inert atmosphere;	100%

3-methoxyphenyl bromide (2398-37-0) + 4-amino-2-(benzyloxy)benzonitrile (284044-40-2) → 4-(3-methoxyphenylamino)-2-benzyloxybenzonitrile

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate In toluene at 100℃; for 31h; Buchwald-Hartwig Coupling;	100%

imidazo[1,2-a]pyridine (274-76-0) + 3-methoxyphenyl bromide (2398-37-0) → 3-(3-methoxyphenyl)imidazo[1,2-a]pyridine (1338248-69-3)

Conditions	Yield
With C27H22N4O2Pd; potassium acetate In N,N-dimethyl acetamide at 140℃; for 18h; Catalytic behavior; Schlenk technique; Inert atmosphere;	100%
With palladium diacetate; potassium hydroxide In water at 100℃; for 24h; Inert atmosphere;	53%

3-methoxyphenyl bromide (2398-37-0) + (2-cyclopropylethynyl)trimethylsilane (81166-84-9) → 1-(2-cyclopropylethynyl)-3-methoxybenzene (445424-01-1)

Conditions	Yield
Stage #1: 3-methoxyphenyl bromide With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; cesium fluoride In water at 20℃; for 0.25h; Sealed tube; Inert atmosphere; Stage #2: (2-cyclopropylethynyl)trimethylsilane In water at 80℃; for 16h; Sealed tube; Inert atmosphere;	100%

1H-imidazole (288-32-4) + 3-methoxyphenyl bromide (2398-37-0) → 1-(3-methoxyphenyl)-1H-imidazole (10040-94-5)

Conditions	Yield
With potassium phosphate; copper(l) iodide; L-lysine at 130℃; for 5h; Microwave irradiation;	99%
With copper(l) iodide; N-((4-nitro-1-oxy-pyridin-2-yl)methyl)oxalamic acid; tetrabutylammomium bromide; potassium hydroxide In water at 100℃; for 36h; Schlenk technique; Inert atmosphere; Sealed tube;	99%
With potassium tert-butylate; copper(I) oxide In N,N-dimethyl-formamide at 130℃; for 24h;	91%

N-Methylformamide (123-39-7) + 3-methoxyphenyl bromide (2398-37-0) → N-methyl-N-(3-methoxyphenyl)carboxamide (14924-70-0)

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 16h;	99%
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 16h; Arylation;	98%

3-methoxyphenyl bromide (2398-37-0) + bis(pinacol)diborane (73183-34-3) → 2-(3-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (401797-04-4)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1-(4,4'-di-tert-butyl-[2,2'-bipyridin]-6-yl)-2-(dimethyl(phenyl)silyl)-2,3-dihydro-1H-benzo[d][1,3,2]diazaborole Inert atmosphere; Schlenk technique; Sealed tube;	99%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; cyclopentyl methyl ether; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole at 100℃; for 16h; Schlenk technique; Inert atmosphere;	96%
With Pinacolborane; 4,4'-di-tert-butylbipyridine In cyclohexane at 80℃;	77%

3-methoxyphenyl bromide (2398-37-0) + 4-methylphenylboronic acid (5720-05-8) → 3-methoxy-4'-methylbiphenyl (24423-07-2)

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 25℃; for 1h; Catalytic behavior; Suzuki Coupling; Microwave irradiation;	99%
With caesium carbonate; [PdCl(NNCNHC-nBu)]BF4 In water; N,N-dimethyl-formamide at 80℃; for 2h; Suzuki-Miyaura reaction;	95%
With potassium phosphate; N-[(4-diphenylphosphinophenyl)methyl] D-gluconamide; PdCl2(GLCAphos)2 In water at 80℃; for 16h;	93%

morpholine (110-91-8) + 3-methoxyphenyl bromide (2398-37-0) → 4-(3-methoxyphenyl)morpholine (32040-09-8)

Conditions	Yield
With [Pd(N,N'-bis(2,6-bis(di-p-tolylmethyl)-4-methylphenyl)-imidazol-2-ylidene)(acetylacetonate)Cl]; lithium hexamethyldisilazane In 1,4-dioxane at 110℃; for 3h; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube;	99%
With sodium t-butanolate; palladium diacetate In toluene at 80℃; for 0.5h; Buchwald-Hartwig amination;	98%
With C27H34N5P; sodium hydroxide; bis(dibenzylideneacetone)-palladium(0) In tert-Amyl alcohol at 100℃; Inert atmosphere;	97.77%

3-methoxyphenyl bromide (2398-37-0) + 1-Naphthylboronic acid (13922-41-3) → 1-(3-methoxybiphenyl)naphthalene (27331-43-7)

Conditions	Yield
With potassium fluoride; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 18h; Suzuki coupling;	99%
With KF; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In 1,2-dioxacyclohexane	99%
With potassium phosphate In ethanol; water at 20℃; for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Green chemistry;	98%
With ethyl 2-hydroxypropionate; palladium diacetate; potassium carbonate In water at 80℃; for 2h; Suzuki-Miyaura Coupling; Green chemistry;	50%
With Br(1-)*C25H29BrN5O6(1+); potassium carbonate In water at 100℃; for 2h; Suzuki-Miyaura coupling;	> 99 %Spectr.

3-methoxyphenyl bromide (2398-37-0) + 2-Methylphenylboronic acid (16419-60-6) → 3'-methoxy-2-methyl-1,1'-biphenyl (135227-03-1)

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 30℃; for 2h; Catalytic behavior; Temperature; Time; Suzuki Coupling; Microwave irradiation;	99%
With C20H12N2O8PdS2(2-)*2Na(1+); sodium hydroxide In water at 100℃; for 3h;	95%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water for 24h; Heating;	90%

3-methoxyphenyl bromide (2398-37-0) → 3-methoxyphenyl azide (3866-16-8)

Conditions	Yield
With sodium azide In ethylene glycol at 100℃; for 3h; Green chemistry;	99%
With copper(l) iodide; sodium azide; sodium L-ascorbate; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In ethanol for 0.666667h; Heating;	95%
With copper(l) iodide; sodium azide; L-proline; sodium hydroxide In ethanol at 95℃; for 24h;	92%

pyrrolidine (123-75-1) + 3-methoxyphenyl bromide (2398-37-0) → 1-(3-methoxyphenyl)pyrrolidine (32040-07-6)

Conditions	Yield
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 90℃; for 31h;	99%
With potassium phosphate; copper(l) iodide; N-((1-oxy-pyridin-2-yl)methyl)oxalamic acid In dimethyl sulfoxide at 80℃; for 48h; Schlenk technique; Inert atmosphere; Sealed tube; chemoselective reaction;	71%
With 8-Hydroxyquinoline-N-oxide; caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 50℃; for 60h; Ullmann coupling; Inert atmosphere; Sealed tube; chemoselective reaction;

3-methoxyphenyl bromide (2398-37-0) + phenylacetylene (536-74-3) → 1-methoxy-3-(phenylethynyl)benzene (37696-01-8)

Conditions	Yield
With copper(l) iodide; ethanolamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; water at 60℃; for 26h; Sonogashira coupling;	99%
With UC Pd; potassium carbonate; XPhos In ethanol; water at 50℃; for 5h; Sonogashira coupling; Inert atmosphere;	95%
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine In 1,4-dioxane at 105℃; for 20h; Sonogashira coupling; Inert atmosphere;	94%

3-methoxyphenyl bromide (2398-37-0) + Pentafluorobenzene (363-72-4) → 2,3,4,5,6-pentafluoro-3'-methoxy-1,1'-biphenyl (198975-36-9)

Conditions	Yield
With potassium phosphate; chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II); Trimethylacetic acid In N,N-dimethyl acetamide at 80℃; Glovebox;	99%
With potassium phosphate; chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)] palladium(II); Trimethylacetic acid In N,N-dimethyl acetamide at 80℃; for 2 - 4h;	98%
With [Pd(trifluoroacetato)2(1,3-diisopropylbenzimidazolin-2-ylidene)(C2N3CH2Ph3)]; potassium carbonate In N,N-dimethyl acetamide at 120℃; for 24h;	95%

3-methoxyphenyl bromide (2398-37-0) + benzene (71-43-2) → 3-methoxybiphenyl (2113-56-6)

Conditions	Yield
With C34H52Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 120℃; for 16h; Reagent/catalyst;	99%
With pentamethylcyclopentadienyltricarbonylrhenium for 2.5h; Schlenk technique; Inert atmosphere; UV-irradiation;	92%
With potassium tert-butylate at 100℃; for 24h; Inert atmosphere;	89%

3-methoxyphenyl bromide (2398-37-0) → m-Anisidine (536-90-3)

Conditions	Yield
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 80℃; for 5h; Inert atmosphere;	99%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere;	93%
With ammonium hydroxide; copper(l) iodide; diethylenetriaminopentaacetic acid; potassium hydroxide In water at 100℃; for 12h; Sealed tube;	90%

Upstream product

• 536-90-3 m-Anisidine 
• 766-85-8 3-methoxy-1-iodobenzene 
• 1464149-60-7 (2,4,6-trimethylphenyl)(3’-methoxyphenyl)iodonium triflate 
• 67-56-1 methanol 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 77-78-1 dimethyl sulfate 
• 591-20-8 3-Bromophenol 
• 80-48-8 methyl p-toluene sulfonate 
• 586-38-9 3-Methoxybenzoic acid 
• 585-79-5 m-nitrobromobenzene 
• 124-41-4 sodium methylate 
• 616-38-6 carbonic acid dimethyl ester 
• 870485-34-0 (3-methoxyphenyl)(triphenyl-λ5-phosphanyl)gold 
• 578-57-4 2-bromoanisole 

Downstream Products

• 24876-04-8 1-(2-bromo-4-methoxy-phenyl)-propan-1-one 
• 34874-62-9 N-(3-methoxyphenyl)-di-n-butylamine 
• 10040-94-5 1-(3-methoxyphenyl)-1H-imidazole 
• 57816-04-3 methyl 4-(3-methoxyphenyl)butanoate 
• 130028-20-5 methyl (E)-4-(3-methoxyphenyl)but-3-enoate 
• 50900-49-7 2-<(3-methoxyphenyl)thio>benzoic acid 
• 57800-65-4 (3-methoxyphenyl)(o-tolyl)methanone 
• 16123-41-4 2-methyl-3-(3-methoxy-phenyl)propan-1-ol 
• 66916-97-0 2-bromo-4-methoxybenzyl chloride 
• 40463-20-5 1-methoxy-3-(pent-4-en-1-yl)benzene 
• 67437-02-9 1,1,5,5-Tetrakis-(m-methoxyphenyl)-3,3-dimethyl-4-penten-1-ol 
• 92587-68-3 4-(3-methoxyphenyl)-but-3-yn-1-ol 
• 101651-37-0 N-(3-methoxyphenyl)acetanilide 
• 5368-81-0 methyl 3-methoxybenzoate 

Relevant articles and documents

One-step preparation of some 3-substituted anisoles

A one-step preparation of 3-bromoanisole, 3-chloroanisole, and 3-trifluoromethylanisole from the corresponding 3-substituted nitrobenzenes is carried out by nucleophilic aromatic substitution of the nitro group with sodium or potassium methoxide, employing an effective amount of a phase-transfer catalyst (PTC), in a medium of a nonpolar aprotic solvent, under aerobic conditions, at a temperature of 50-65°C. The alkali methoxide used can be a pre-prepared solid, or it can be prepared in situ from the alkali hydroxide and methanol. The methoxydenitration proved to be very sensitive to the type of PTC. The effect of the solvent on the reaction is discussed. The targeted anisoles are obtained in yields of more than 80% and purities of greater than 99%.

Nickel-Catalyzed Photodehalogenation of Aryl Bromides

Herein, we describe a Ni-catalyzed photodehalogenation of aryl bromides under visible-light irradiation that utilizes tetrahydrofuran as hydrogen source. The protocol obviates the need for exogeneous amine reductants or photocatalysts and is characterized by its simplicity and broad scope, including challenging substrate combinations.

One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides

A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a SRN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.