620-13-3

Basic information

• Product Name: 3-Methylbenzyl bromide
• Synonyms: 1-(bromomethyl)-3-methyl-benzen;alpha-bromo-m-xylen;Benzene, 1-(bromomethyl)-3-methyl-;bromo-xylene;m-(Bromomethyl)toluene;m-Xylene, alpha-bromo-;omega-bromo-m-xylene;1-(BROMOMETHYL)-3-METHYLBENZENE
• CAS NO: 620-13-3
• Molecular Formula: C₈H₉Br
• Molecular Weight: 185.06
• EINECS: 210-625-2
• Product Categories: Methyl Halides;Phenyls & Phenyl-Het;Benzyl;Methyl Halides;Phenyls & Phenyl-Het;Aryl;Building Blocks;C8;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 620-13-3.mol
• Article Data: 31

Chemical Properties

• Melting Point: -20.49°C (estimate)
• Boiling Point: 185 °C340 mm Hg(lit.)
• Flash Point: 180 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.37 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.264mmHg at 25°C
• Refractive Index: n20/D 1.566(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: practically insoluble
• Merck: 14,10090
• BRN: 2076425
• CAS DataBase Reference: 3-Methylbenzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methylbenzyl bromide(620-13-3)
• EPA Substance Registry System: 3-Methylbenzyl bromide(620-13-3)

Safety Data

• Hazard Codes: C
• Statements: 20/22-34-20/21/22
• Safety Statements: 26-27-36/37/39-45-7/9
• RIDADR: UN 1701 6.1/PG 2
• WGK Germany: 3
• RTECS: CY9039200
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 620-13-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

InChI:InChI=1/C8H9Br/c1-7-3-2-4-8(5-7)6-9/h2-5H,6H2,1H3

Synthetic route

→ 1-bromomethyl-3-methyl-benzene (620-13-3)

Conditions	Yield
With N-Bromosuccinimide; trityl tetrafluoroborate In dichloromethane; benzene at 20℃; Irradiation; Inert atmosphere; chemoselective reaction;	92%
With dibenzoyl peroxide In ethyl acetate for 3.5h; Reflux;	75%
With hydrogen bromide; dihydrogen peroxide In water at 0℃; Incandescent lamp light;	71.1%

m-tolyl aldehyde (620-23-5) → 1-bromomethyl-3-methyl-benzene (620-13-3)

Conditions	Yield
With bromine; trimethylamine borane In chloroform at 0 - 5℃; for 0.0333333h;	92%
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 0.5 h / 20 °C 2: phosphorus tribromide / dichloromethane / 0.5 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol / 0.17 h / 0 °C 2: phosphorus tribromide / diethyl ether / 3 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 2 h / 0 °C 2: phosphorus tribromide / diethyl ether / 0.5 h / 0 °C View Scheme

m-xylene (108-38-3) → 1-bromomethyl-3-methyl-benzene (620-13-3) + 1,3-bis-(bromomethyl)benzene (626-15-3)

Conditions	Yield
With hydrogen bromide; dihydrogen peroxide In water at 20℃; Irradiation;	A 73% B 11%
With N-Bromosuccinimide for 0.15h; microwave irradiation;	A 40% B 42%
With bromine In water Irradiation;	A 40 % Chromat. B 53 % Chromat.

m-xylene (108-38-3) → 1-bromo-2,4-dimethylbenzene (583-70-0) + 1-bromomethyl-3-methyl-benzene (620-13-3)

Conditions	Yield
With sodium bromate; sodium hydrogensulfite In cyclohexane; water at 20℃; for 4h; Bromination;	A 1% B 64%
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 4h; Bromination;	A 57% B n/a
With N-Bromosuccinimide at 150℃; under 2625.26 Torr; for 0.0666667h; microwave irradiation;	A 1.5 % Chromat. B 56 % Chromat.

3-methylbenzyl Co(III)(dmgH)2py (36583-13-8) + Bromotrichloromethane (75-62-7) → bromo Co(III)(dmgH)2py + hexachloroethane (67-72-1) + 1-bromomethyl-3-methyl-benzene (620-13-3) + 1-Methyl-3-(2,2,2-trichloro-ethyl)-benzene

Conditions	Yield
In chloroform Excess of CHCl3, 55°C for 5 h;; detected by NMR spectra and GLC;;	A n/a B n/a C 45% D 55%

m-MeC6H4CH2Co(dmgH)2Py → 1-bromomethyl-3-methyl-benzene (620-13-3) + 1-bromo-2-(bromomethyl)-4-methylbenzene (27561-50-8)

Conditions	Yield
With bromine In chloroform Ambient temperature;	A 50% B 50%

m-methylbenzyl-p-methylphenyldimethylammonium bromide → 1-bromomethyl-3-methyl-benzene (620-13-3) + Dimethyl-p-toluidine (99-97-8)

Conditions	Yield
In acetone at 45℃; Rate constant; Equilibrium constant;

m-methylbenzyl-m-methylphenyldimethylammonium bromide → N,N-dimethyl-m-toluidine (121-72-2) + 1-bromomethyl-3-methyl-benzene (620-13-3)

Conditions	Yield
In acetone at 45℃; Rate constant; Equilibrium constant;

m-methylbenzyl-p-bromophenyldimethylammonium bromide → 1-bromomethyl-3-methyl-benzene (620-13-3) + 4-bromo-N,N-dimethylaniline (586-77-6)

Conditions	Yield
In acetone at 45℃; Rate constant; Equilibrium constant;

m-methylbenzyl-m-chlorophenyldimethylammonium bromide → 1-bromomethyl-3-methyl-benzene (620-13-3) + 3-chloro-N,N-dimethylaniline (6848-13-1)

Conditions	Yield
In acetone at 45℃; Rate constant; Equilibrium constant;

m-xylene (108-38-3) + 1 mol tetrabromomethane → 1-bromomethyl-3-methyl-benzene (620-13-3)

Conditions	Yield
at 150 - 180℃;

bromine (7726-95-6) + m-xylene (108-38-3) → 1-bromomethyl-3-methyl-benzene (620-13-3) + 1,3-bis-(bromomethyl)benzene (626-15-3)

bromine (7726-95-6) + m-xylene (108-38-3) → 1-bromomethyl-3-methyl-benzene (620-13-3) + 1,3-bis-(bromomethyl)benzene (626-15-3) + ω.ω.ω'.ω'-tetrabromo-1.3-dimethyl-benzene

Conditions	Yield
im Sonnenlicht;

bromine (7726-95-6) + m-xylene (108-38-3) → 1-bromomethyl-3-methyl-benzene (620-13-3) + 1,3-bis-(bromomethyl)benzene (626-15-3) + ω.ω.ω'-tribromo-m-xylene

tetrachloromethane (56-23-5) + 3,5-dimethylenecyclohexene (38461-17-5) + bromine (7726-95-6) + sodium hydrogencarbonate → 1-bromomethyl-3-methyl-benzene (620-13-3) + 1,3-bis-(bromomethyl)benzene (626-15-3)

bromocyane (506-68-3) + N-benzyl-N-methyl-1-(m-tolyl)methanamine (20441-10-5) → 1-bromomethyl-3-methyl-benzene (620-13-3) + N-benzyl-N-methyl cyanamide (34065-04-8) + methyl-benzyl-bis-<3-methyl-benzyl>-ammonium bromide

Bromotrichloromethane (75-62-7) + <3-MeC6H4CH2Co(dmgH)2Py> → 1-bromomethyl-3-methyl-benzene (620-13-3) + 1-Methyl-3-(2,2,2-trichloro-ethyl)-benzene

Conditions	Yield
With 1H-imidazole In chloroform at 70℃; for 3h; Title compound not separated from byproducts;

triethyl borate (150-46-9) + carbon monoxide (201230-82-2) + 1-bromomethyl-3-methyl-benzene (620-13-3) → ethyl m-methylphenylacetate (40061-55-0)

Conditions	Yield
1,5-hexadienerhodium(I)-chloride dimer at 75℃; under 760 Torr; Heating; overnight; other solvent;	100%

tri-n-propyl borate (688-71-1) + carbon monoxide (201230-82-2) + 1-bromomethyl-3-methyl-benzene (620-13-3) → m-Tolyl-acetic acid propyl ester (93579-00-1)

Conditions	Yield
1,5-hexadienerhodium(I)-chloride dimer at 75℃; under 760 Torr; Heating; overnight; other solvent;	100%

tris(trimethylsilyl) phosphite (1795-31-9) + 1-bromomethyl-3-methyl-benzene (620-13-3) → bis(trimethylsilyl) 3-methylbenzylphosphonate (368454-35-7)

Conditions	Yield
In toluene at 95℃; for 4h; Michaelis-Arbuzov reaction;	100%
In toluene at 95℃; for 4h; Michaelis-Arbuzov reaction;	100 % Spectr.

1-bromomethyl-3-methyl-benzene (620-13-3) + 2,3-bis(methoxycarbonyl)phenol (36669-02-0) → 3-(3-methyl-benzyloxy)-phthalic acid dimethyl ester (1061605-99-9)

Conditions	Yield
With potassium carbonate In acetone Heating / reflux;	100%

N-[4-(2-amino-4-hydroxy-phenylsulfanyl)-phenyl]-acetamide (943620-65-3) + 1-bromomethyl-3-methyl-benzene (620-13-3) → N-{4-[2-amino-4-(3-methyl-benzyloxy)-phenylsulfanyl]-phenyl}-acetamide (943617-50-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h;	100%

1-bromomethyl-3-methyl-benzene (620-13-3) + 4-nitro-aniline (100-01-6) → bis(3-methylbenzyl)(4-nitrophenyl)amine (1032373-71-9)

Conditions	Yield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;	100%

1-bromomethyl-3-methyl-benzene (620-13-3) + 1-hydroxy-3,6,7-tris(methoxymethoxy)-9H-xanthen-9-one (1314917-55-9) → C27H28O9 (1314917-77-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 6h;	100%

1-bromomethyl-3-methyl-benzene (620-13-3) + methyl 3-chloro-1H-indole-4-carboxylate → C18H16ClNO2

Conditions	Yield
With sodium hydride at 0℃; for 5h;	100%

4-nitro-1H-indoIe (4769-97-5) + 1-bromomethyl-3-methyl-benzene (620-13-3) → C16H14N2O2

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 3.15h;	100%

1-bromomethyl-3-methyl-benzene (620-13-3) + triphenylphosphine (603-35-0) → (3-methylbenzyl)(triphenyl)phosphonium bromide (1702-41-6)

Conditions	Yield
In chloroform for 2h; Heating;	99%

1-bromomethyl-3-methyl-benzene (620-13-3) + 3,6-Diisopropyl-2-pyrazinethiol (86799-80-6) → 2-(3-methylbenzylthio)-3,6-diisopropylpyrazine (120061-26-9)

Conditions	Yield
With sodium carbonate	99%

1-bromomethyl-3-methyl-benzene (620-13-3) + (3-Hydroxy-propyl)-[2-((3-methyl-benzyl)-{6-[(3-trifluoromethyl-benzylamino)-methyl]-pyridin-2-ylmethyl}-amino)-ethyl]-carbamic acid tert-butyl ester (204196-32-7) → (3-Hydroxy-propyl)-{2-[(3-methyl-benzyl)-(6-{[(3-methyl-benzyl)-(3-trifluoromethyl-benzyl)-amino]-methyl}-pyridin-2-ylmethyl)-amino]-ethyl}-carbamic acid tert-butyl ester (204196-35-0)

Conditions	Yield
With potassium carbonate In acetonitrile Ambient temperature;	99%

2-bromo-pyridin-3-ol (6602-32-0) + 1-bromomethyl-3-methyl-benzene (620-13-3) → 2-bromo-3-((3-methylbenzyl)oxy)pyridine

Conditions	Yield
With potassium carbonate In acetonitrile at 60℃; for 15.5h;	99%

1-bromomethyl-3-methyl-benzene (620-13-3) + 4-(3-methyl-5-oxo-4H-pyrazol-1-yl)-N-(pyridine-4-ylmethyl)benzamide → 4-({[4-(3-methyl-5-oxo-4H-pyrazol-1-yl)phenyl]formamido}methyl)-1-[(3-methylphenyl)methyl]pyridin-1-ium bromide

Conditions	Yield
In N,N-dimethyl-formamide at 40 - 50℃;	98.3%

methyl N-[4'-(trifluoromethoxy)biphenyl-4-yl]oxamate (1019996-87-2) + 1-bromomethyl-3-methyl-benzene (620-13-3) → methyl N-(3-methylbenzyl)-N-[4'-(trifluoromethoxy)biphenyl-4-yl]oxamate (1019996-90-7)

Conditions	Yield
With potassium carbonate; 18-crown-6 ether In acetonitrile at 50℃; for 3h;	98%
With 18-crown-6 ether; potassium carbonate In acetonitrile at 50℃; for 3h; Inert atmosphere;	98%

1-bromomethyl-3-methyl-benzene (620-13-3) + phenyltriisopropoxytitanium(IV) (16635-23-7) → 1-methyl-3-(phenylmethyl)-benzene (620-47-3)

Conditions	Yield
With palladium diacetate; Tri(p-tolyl)phosphine In toluene at 25℃; for 2h; Inert atmosphere;	98%

1-bromomethyl-3-methyl-benzene (620-13-3) + phenylacetylene (536-74-3) → 1-(3-methyl-benzyl)-4-phenyl-1H-[1,2,3]triazole

Conditions	Yield
With sodium azide In water at 23 - 25℃; for 24h; Inert atmosphere; Schlenk technique; Green chemistry;	98%

8-chlorotheophylline (85-18-7) + 1-bromomethyl-3-methyl-benzene (620-13-3) → 8-chloro-1,3-dimethyl-7-(3-methylbenzyl)-1H-purine-2,6-(3H,7H)-dione

Conditions	Yield
Stage #1: 8-chlorotheophylline With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 1-bromomethyl-3-methyl-benzene In N,N-dimethyl-formamide at 20 - 60℃; for 2.5h;	98%
Stage #1: 8-chlorotheophylline With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 1-bromomethyl-3-methyl-benzene In N,N-dimethyl-formamide at 20 - 60℃; for 2.5h;	98%

1-bromomethyl-3-methyl-benzene (620-13-3) + 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester (6093-71-6) → ethyl 7-((3-methylbenzyl)oxy)-2-oxo-2H-chromene-3-carboxylate

Conditions	Yield
Stage #1: 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-bromomethyl-3-methyl-benzene In N,N-dimethyl-formamide at 20℃; for 48h;	98%

1-bromomethyl-3-methyl-benzene (620-13-3) + MANDELIC ACID (611-71-2, 611-72-3, 17199-29-0, 90-64-2) → 3-methylbenzyl 2-oxo-2-phenylacetate

Conditions	Yield
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; 5,10,15,20-tetraphenyl-21H,23H-porphine; bis(triphenylphosphane)copper(I) nitrate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 80℃; for 10h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst;	97.7%

methanol (67-56-1) + 1-bromomethyl-3-methyl-benzene (620-13-3) → α-methoxy-m-xylene (7116-51-0)

Conditions	Yield
With silver(II) oxide for 0.5h; Heating;	97%

1-bromomethyl-3-methyl-benzene (620-13-3) + 7-(tert-butoxycarbonyl)-3,7,12,18-tetraazabicyclo[12.3.1]octadeca-1(18),14,16-triene (182576-19-8) → 3,12-Bis-(3-methyl-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1(18),14,16-triene-7-carboxylic acid tert-butyl ester (189182-04-5)

Conditions	Yield
With potassium carbonate In acetonitrile Ambient temperature;	97%

1-bromomethyl-3-methyl-benzene (620-13-3) + (3-Hydroxy-propyl)-[2-((3-trifluoromethyl-benzyl)-{6-[(3-trifluoromethyl-benzylamino)-methyl]-pyridin-2-ylmethyl}-amino)-ethyl]-carbamic acid tert-butyl ester (204196-39-4) → (3-Hydroxy-propyl)-{2-[(6-{[(3-methyl-benzyl)-(3-trifluoromethyl-benzyl)-amino]-methyl}-pyridin-2-ylmethyl)-(3-trifluoromethyl-benzyl)-amino]-ethyl}-carbamic acid tert-butyl ester (204196-42-9)

Conditions	Yield
With potassium carbonate In acetonitrile Ambient temperature;	97%

1-bromomethyl-3-methyl-benzene (620-13-3) → 1-(azidomethyl)-3-methylbenzene (126799-82-4)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 20 - 80℃; for 4h;	97%
With sodium azide In dimethyl sulfoxide at 20℃; for 24h;	94%
With sodium azide In water; acetone at 20 - 60℃;

1-bromomethyl-3-methyl-benzene (620-13-3) + potassium phenyltrifluoborate → 1-methyl-3-(phenylmethyl)-benzene (620-47-3)

Conditions	Yield
With [Pd(N-(3-chloro-2-quinoxalinyl)-N'-(2,6-diisopropylphenyl)imidazolium)(PPh3)Cl2]; potassium carbonate In water at 70℃; for 3h; Catalytic behavior; Suzuki-Miyaura Coupling;	97%

bis(4-hydroxyphenyl)disulfide (15015-57-3) + 1-bromomethyl-3-methyl-benzene (620-13-3) → C28H26O2S2

Conditions	Yield
With potassium carbonate In acetone at 60℃; Inert atmosphere;	97%

1-bromomethyl-3-methyl-benzene (620-13-3) + 4-n-methylphenylacetylene (766-97-2) → 1-(3-methylbenzyl)-4-(p-tolyl)-1H-1,2,3-triazole

Conditions	Yield
With sodium azide In methanol; water at 70℃; for 4h;	97%

1-bromomethyl-3-methyl-benzene (620-13-3) + 6-methoxy-1-(pyridin-2-yl)-9H-pyrido[3,4-b]indole → 1-pyridin-2-yl-6-methoxy-9-(3-methylbenzyl)-β-carboline

Conditions	Yield
With palladium diacetate; caesium carbonate; silver(l) oxide In acetonitrile at 55℃;	96.2%
Stage #1: 6-methoxy-1-(pyridin-2-yl)-9H-pyrido[3,4-b]indole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 1-bromomethyl-3-methyl-benzene In N,N-dimethyl-formamide at 20℃; for 0.333333h; Temperature; Concentration;	85.8%

para-xylene (106-42-3) + 1-bromomethyl-3-methyl-benzene (620-13-3) → 1,4-dimethyl-2-(3-methylbenzyl) benzene (61819-81-6)

Conditions	Yield
With indium(III) chloride; 4 A molecular sieve In dichloromethane at 20℃; for 16h; Friedel-Crafts alkylation;	96%

1-bromomethyl-3-methyl-benzene (620-13-3) + phenylacetylene (536-74-3) → 1‐(3‐methylbenzyl)‐4‐phenyl‐1H‐1,2,3‐triazole (126800-03-1)

Conditions	Yield
With sodium azide In methanol; water at 70℃; for 2h;	96%
With choline azide at 75℃; for 0.416667h; Green chemistry;	95%
With sodium azide In water for 0.333333h; Reflux; regioselective reaction;	91%

Upstream product

• 7726-95-6 bromine 
• 108-38-3 m-xylene 
• 106-42-3 para-xylene 
• 36583-13-8 3-methylbenzyl Co(III)(dmgH)2py 
• 75-62-7 Bromotrichloromethane 
• 103668-90-2 2-oxatricyclo<2.2.2.0^3,5>octan-6-one 
• 108-24-7 acetic anhydride 
• 80582-76-9 (1S,2S)-cyclohex-4-ene-1,2-diol 
• 506-68-3 bromocyane 
• 20441-10-5 N-benzyl-N-methyl-1-(m-tolyl)methanamine 
• 56-23-5 tetrachloromethane 
• 38461-17-5 3,5-dimethylenecyclohexene 
• 620-23-5 m-tolyl aldehyde 
• 103668-92-4 6-methyl-2-oxatricyclo<2.2.2.0^3,5>octan-6-ol 

Downstream Products

• 5321-48-2 1-(3-methylbenzyl)piperazine 
• 23879-32-5 N,N,3-trimethylbenzylamine 
• 1702-41-6 (3-methylbenzyl)(triphenyl)phosphonium bromide 
• 7116-51-0 α-methoxy-m-xylene 
• 40677-59-6 3-methylbenzyl tert-butyl ether 
• 40061-55-0 ethyl m-methylphenylacetate 
• 621-36-3 m-methylphenylacetic acid 
• 4662-96-8 1,2-di-m-tolylethane 
• 83598-09-8 1,3-bis(3-methylphenyl)propan-3-one 
• 88364-53-8 m-Tolyl-acetic acid 3-methyl-benzyl ester 
• 145243-34-1 2-(Benzhydrylidene-amino)-3-m-tolyl-propionic acid methyl ester 
• 120013-05-0 N-Methyl-N-{2-[1-(3-methyl-benzyl)-piperidin-4-yl]-ethyl}-benzamide 
• 76698-70-9 3-methylbenzyl selenocyanate 
• 130849-40-0 [1-(Dimethyl-phosphinoyl)-2-m-tolyl-ethyl]-[1-phenyl-meth-(E)-ylidene]-amine 

Relevant articles and documents

Synthesis, Docking, and Biological activities of novel Metacetamol embedded [1,2,3]-triazole derivatives

ERα controls the breast tissue development and progression of breast cancer. In our search for novel compounds to target Estrogen Receptor Alpha Ligand-Binding Domain, we identified “N-(3-((1H-1,2,3-triazol-4-yl)methoxy)phenyl)acetamide” derivatives as lead compounds. The Docking studies indicated good docking score for Metacetamol derivatives when docked into the 1XP6. A series of metacetamol derivatives have been synthesized, characterized and evaluated for cytotoxicity, anti bacterial and anti oxidant activities. Among the tested twelve hybrid compounds, “7a, 7g, 7h and 7i” derivatives showed promising cytotoxicity with IC50 value of 50 value of 30 μM, whereas Compounds “7a, 7b, 7c, 7d, 7g, 7j, 7k and 7l” showed moderate anti bacterial activity with the MIC value of 300 μM.

Synthesis of Phenanthridines through Palladium-Catalyzed Cascade Reaction of 2-Halo-N-Ms-arylamines with Benzyl Halides/Sulfonates

An efficient palladium-catalyzed nucleophilic substitution/C–H activation/aromatization cascade reaction between readily available 2-halo-N-Ms-arylamines (Ms = methanesulfonyl) and benzyl halides/sulfonates has been described. A wide variety of phenanthridines were synthesized in a one-pot fashion in moderate to high yields (37–86 %). Notably, this method provides a straightforward, facile approach for the synthesis of phenanthridines. The practicality was further substantiated by successfully carrying out a gram-scale preparation.

Palladium(0)-catalyzed cyclopropanation of benzyl bromides via C(sp 3)-H bond activation

A novel and highly efficient Pd(0)-catalyzed domino reaction to prepare cyclopropane derivatives has been established. The process involves a Heck-type coupling reaction and a C(sp3)-H bond activation. Preliminary DFT calculations suggest that a four-membered palladacycle intermediate is involved. This journal is the Partner Organisations 2014.