877-88-3

Usage

Uses

Used in Organic Synthesis:
3,5-Dimethoxybenzyl bromide is used as a key intermediate in the synthesis of various organic compounds, such as 3,4,3′,5′-tetramethoxystilbene, 3,5-dimethoxyphenylacetic acid, and 1-(3,5-dimethoxyphenyl)-4-pentene. Its presence in these molecules allows for the formation of complex structures and functional groups that are essential in various applications.
Used in Pharmaceutical Synthesis:
3,5-Dimethoxybenzyl bromide is used as a starting material in the multi-step synthesis of resveratrol and 3,5-dimethoxyhomophthalic acid. Resveratrol is a natural polyphenol with antioxidant, anti-inflammatory, and anti-cancer properties, while 3,5-dimethoxyhomophthalic acid is a key intermediate in the synthesis of various pharmaceuticals.
Used in Dimethoxybenzene Alkyl Addition:
3,5-Dimethoxybenzyl bromide is used in the alkyl addition reactions of dimethoxybenzene. This process allows for the formation of new compounds with different functional groups and properties, which can be further utilized in various chemical and pharmaceutical applications.

InChI:InChI=1/C9H11BrO2/c1-11-8-3-7(6-10)4-9(5-8)12-2/h3-5H,6H2,1-2H3

Synthetic route

3,5-dimethoxybenzyl alcohol (705-76-0) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
With phosphorus tribromide In benzene at 20℃;	100%
With phosphorus tribromide In 1,4-dioxane at 40℃; for 1h; Inert atmosphere;	99%
Stage #1: 3,5-dimethoxybenzyl alcohol With triphenylphosphine In dichloromethane at 20℃; for 0.166667h; Appel reaction; Stage #2: With carbon tetrabromide In dichloromethane at -78 - -50℃; Appel reaction;	98%

1,3-Dimethoxy-5-(4-methoxy-benzyloxymethyl)-benzene → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 30℃; for 1.5h;	48%

ethyl 3,5-dimethoxybenzoate (17275-82-0) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
(i) LiAlH4, (ii) PBr3; Multistep reaction;

3,5-dimethoxybenzaldehdye (7311-34-4) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
With phosphorus tribromide In dichloromethane for 1h; Ambient temperature; Yield given;
Multi-step reaction with 2 steps 1: 93 percent / NaBH4 / methanol / 0 °C 2: 89 percent / PBr3 / CH2Cl2 / 12 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: 98 percent / NaBH4 / ethanol 2: 88 percent / PBr3, pyridine / diethyl ether / 1 h View Scheme

(3,5-dimethoxyphenyl)methyl methanesulfonate (192997-46-9) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
With lithium bromide In tetrahydrofuran for 15h; Ambient temperature; Yield given;

methyl 3,5-dimethoxybenzoate (2150-37-0) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
(i) LiAlH4, (ii) PBr3; Multistep reaction;
Multi-step reaction with 2 steps 1: 92 percent / LiAlH4 / diethyl ether 2: 94 percent / PBr3 / CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: HBr / benzene View Scheme

3,5-dimethoxybenzoic acid (1132-21-4) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: LiAlH4 / tetrahydrofuran / 3 h / 20 °C 1.2: 97 percent / Na/K tartrate / tetrahydrofuran / 1 h / 20 °C 2.1: 86 percent / PBr3 / CH2Cl2 / 1 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: SOCl2 2: 92 percent / LiAlH4 / diethyl ether 3: 94 percent / PBr3 / CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1: BH3 / tetrahydrofuran / 2 h / Heating 2: CBr4; tri-n-octylphosphine / diethyl ether / 2 h / 20 °C View Scheme

3,5-Dihydroxybenzoic acid (99-10-5) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: NaOH 2: SOCl2 3: 92 percent / LiAlH4 / diethyl ether 4: 94 percent / PBr3 / CH2Cl2 View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 4 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.17 h / 0 - 20 °C 3.1: triphenylphosphine / dichloromethane / 0.17 h / 20 °C 3.2: -78 - -50 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 4.5 h / 60 °C 2: sodium tetrahydroborate / methanol; tetrahydrofuran / 2.5 h / 70 °C 3: phosphorus tribromide / dichloromethane / 2 h / 20 °C View Scheme

3,5-dimethoxybenzoyl chloride (17213-57-9) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / LiAlH4 / diethyl ether 2: 94 percent / PBr3 / CH2Cl2 View Scheme

3,5-Dihydroxybenzoic acid (99-10-5) + dimethyl sulfate (77-78-1) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
Stage #1: 3,5-Dihydroxybenzoic acid; dimethyl sulfate With potassium carbonate In acetone for 4h; Reflux; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Stage #3: With phosphorus tribromide In dichloromethane at 0 - 20℃;

1,3-dimethoxy-5-methylbenzene (4179-19-5) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 25℃; for 1h; Inert atmosphere;	1.05 g

1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 48 h / 50 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C 3: phosphorus tribromide / tetrahydrofuran / -10 °C View Scheme

3,5-dimethoxybenzyl bromide (877-88-3) + triphenylphosphine (603-35-0) → (3,5-dimethoxybenzyl)triphenylphosphonium bromide (24131-30-4)

Conditions	Yield
In acetonitrile for 4.5h; Reflux;	100%
In benzene for 2h; reflux;	99%
In toluene for 24h; Inert atmosphere; Reflux;	99%

3,5-dimethoxybenzyl bromide (877-88-3) + triethyl phosphite (122-52-1) → diethyl 3,5-dimethoxybenzylphosphonate (108957-75-1)

Conditions	Yield
Esterification; Arbusov reaction;	100%
at 100℃;	98%
In 5,5-dimethyl-1,3-cyclohexadiene for 10h; Michaelis-Arbuzov reaction; Reflux; Inert atmosphere;	96%

3,5-dimethoxybenzyl bromide (877-88-3) + sodium cyanide (143-33-9) → 3,5-dimethoxyphenylacetonitrile (13388-75-5)

Conditions	Yield
In dimethyl sulfoxide at 35 - 40℃; for 1.5h;	100%
In N,N-dimethyl-formamide for 1h;	83%

3,5-dimethoxybenzyl bromide (877-88-3) + vinyl magnesium bromide (1826-67-1) → Methoxyeugenol (64118-89-4)

Conditions	Yield
Stage #1: vinyl magnesium bromide With copper(l) iodide In tetrahydrofuran at -50℃; Stage #2: 3,5-dimethoxybenzyl bromide In tetrahydrofuran at -30 - 20℃;	100%

3,5-dimethoxybenzyl bromide (877-88-3) + methyl 2-cyanoacetate (105-34-0) → cyano-di(3,5-dimethoxy-benzyl)acetic acid methyl ester (1202779-02-9)

Conditions	Yield
Stage #1: methyl 2-cyanoacetate With sodium methylate In methanol at 20℃; Stage #2: 3,5-dimethoxybenzyl bromide In methanol Reflux;	100%

1-(3-methoxyphenethyl)-3,5-bis(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (1006606-32-1) + 3,5-dimethoxybenzyl bromide (877-88-3) → Br(1-)*C37H42NO5(1+) (1187632-62-7)

Conditions	Yield
In acetone at 60℃; Inert atmosphere;	100%

3,5-dimethoxybenzyl bromide (877-88-3) + trimethylsilylacetylene (1066-54-2) → (3-(3,5-dimethoxyphenyl)prop-1-ynyl)trimethylsilane (1394837-78-5)

Conditions	Yield
Stage #1: trimethylsilylacetylene With ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 20℃; for 0.5h; Stage #2: With copper(I) bromide In tetrahydrofuran; diethyl ether at 20℃; for 0.25h; Stage #3: 3,5-dimethoxybenzyl bromide In tetrahydrofuran; diethyl ether at 66℃;	100%

5-hydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one (1043429-55-5) + 3,5-dimethoxybenzyl bromide (877-88-3) → 5-(3,5-dimethoxybenzyloxy)-6-methoxy-2-methylisoquinolin-1(2H)-one (1043429-21-5)

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

3,5-dimethoxybenzyl bromide (877-88-3) + dimethyl (prop-2-yn-1-yl)malonate (95124-07-5) → dimethyl 2-(3,5-dimethoxybenzyl)-2-(prop-2-yn-1-yl)malonate

Conditions	Yield
Stage #1: dimethyl (prop-2-yn-1-yl)malonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: 3,5-dimethoxybenzyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; for 20h; Inert atmosphere;	100%

5-(hydroxymethyl)benzene-1,3-diol (29654-55-5) + 3,5-dimethoxybenzyl bromide (877-88-3) → 3,5-bis(3,5-dimethoxybenzyloxy)benzyl alcohol (176650-92-3)

Conditions	Yield
With dibenzo-18-crown-6; potassium carbonate In acetone for 36h; Inert atmosphere; Reflux;	99%

3,5-dihydroxybenzaldehyde (26153-38-8) + 3,5-dimethoxybenzyl bromide (877-88-3) → 3,5-bis-(3,5-dimethoxy-benzyloxy)-benzaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 1.5h;	99%
With potassium carbonate In N,N-dimethyl-formamide Inert atmosphere; Schlenk technique;	77%

triethyl phosphate (78-40-0) + 3,5-dimethoxybenzyl bromide (877-88-3) → diethyl 3,5-dimethoxybenzylphosphonate (108957-75-1)

Conditions	Yield
at 160℃; for 4h;	99%
at 120℃; for 10h;	95%
at 160℃; for 4h;	95%

3,5-dimethoxybenzyl bromide (877-88-3) + quinindine (56-54-2, 130-95-0, 572-59-8, 572-60-1, 42151-59-7, 47342-58-5, 72402-50-7, 72402-51-8, 72402-52-9, 72402-53-0, 101143-86-6, 101143-87-7, 101143-88-8, 146925-10-2) → C29H35N2O4(1+)*Br(1-)

Conditions	Yield
In toluene at 80℃; for 2h;	99%

3,5-dimethoxybenzyl bromide (877-88-3) + diothiothreitol (3483-12-3, 6892-68-8, 7634-42-6, 16096-97-2, 27565-41-9, 35454-97-8) → 1,4-bis-(3,5-dimethoxy-benzylsulfanyl)-butane-2,3-diol

Conditions	Yield
Stage #1: diothiothreitol With sodium hydroxide In ethanol Stage #2: 3,5-dimethoxybenzyl bromide In tetrahydrofuran; ethanol at 20℃; for 5h;	98%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + 3,5-dimethoxybenzyl bromide (877-88-3) → N,N'-ethane-1,2-diyl N,N'-bis(3,5-dimethoxybenzyloxy) N,N,N',N'-tetramethylammonium dibromide

Conditions	Yield
In N,N-dimethyl-formamide at 70℃; Inert atmosphere;	98%
In N,N-dimethyl-formamide at 70℃; for 15h; Inert atmosphere;	98%

3,5-dimethoxybenzyl bromide (877-88-3) + phenylacetylene (536-74-3) → 1-(3,5-dimethoxybenzyl)-4-phenyl-1H-1,2,3-triazole

Conditions	Yield
With sodium azide; CuNPs/C In water at 70℃; for 4h;	98%
With sodium azide; copper nanoparticles on activated carbon In water at 70℃; for 4h; regioselective reaction;	98%
With sodium azide at 50℃; for 48h;	89%
With sodium azide In water at 80℃; for 6h;	86%

2,2,4,4-tetramethylpentane-1,3-diol (33950-45-7) + 3,5-dimethoxybenzyl bromide (877-88-3) → 1-(3,5-dimethoxybenzyloxy)-2,2,4,4-tetramethylpentan-3-ol (1313999-66-4)

Conditions	Yield
Stage #1: 2,2,4,4-tetramethylpentane-1,3-diol With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0℃; for 0.75h; Inert atmosphere; Stage #2: 3,5-dimethoxybenzyl bromide In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 20℃; for 5h;	97%

3,5-dimethoxybenzyl bromide (877-88-3) + N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → (S)-tert-butyl N-(diphenylmethylene)-(3,5-dimethoxyphenyl)alaninate

Conditions	Yield
With C37H37N2O(1+)*Br(1-); potassium hydroxide In chloroform; water; toluene at -40℃; for 72h; enantioselective reaction;	97%

3,5-dimethoxybenzyl bromide (877-88-3) + C11H13F3O3SZn → 1-(4-tert-butylbenzyl)-3,5-dimethoxybenzene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl acetamide at 60℃; for 24h; Inert atmosphere; Schlenk technique;	97%

3,5-dimethoxybenzyl bromide (877-88-3) → (E)-3,3',5,5'-tetramethoxystilbene (80715-09-9, 125910-10-3, 125910-07-8)

Conditions	Yield
With Benzyl phenyl selenoxide; potassium hexamethylsilazane In toluene at 25℃; for 4h; Inert atmosphere;	96%
With lithium diisopropyl amide In tetrahydrofuran; hexane a.) -50 deg C, 30 min, b.) RT, 1.5 h;	69%
Multi-step reaction with 2 steps 1: tetrabutylammonium iodide / 110 - 130 °C 2: sodium hydride / dimethylformamide / 20 °C View Scheme

3,5-dimethoxybenzyl bromide (877-88-3) + phenyltriisopropoxytitanium(IV) (16635-23-7) → (3,5-dimethoxyphenyl)phenylmethane (52692-17-8)

Conditions	Yield
With palladium diacetate; Tri(p-tolyl)phosphine In toluene at 60℃; for 2h; Inert atmosphere;	96%

4,4'-bipyridine (553-26-4) + 3,5-dimethoxybenzyl bromide (877-88-3) → C28H30N2O4(2+)*2Br(1-)

Conditions	Yield
In N,N-dimethyl-formamide at 55℃; for 96h;	96%

3,5-dimethoxybenzyl bromide (877-88-3) + C54H68N2O11 → C72H88N2O15

Conditions	Yield
With potassium carbonate In chloroform for 24h; Reflux;	96%

3,5-dimethoxybenzyl bromide (877-88-3) + malononitrile (109-77-3) → C21H22N2O4

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 2h; Green chemistry;	96%

silver(I) trifluoromethoxide (1006904-72-8) + 3,5-dimethoxybenzyl bromide (877-88-3) → 1,3-dimethoxy-5-((trifluoromethoxy)methyl)benzene

Conditions	Yield
Stage #1: 3,5-dimethoxybenzyl bromide In acetonitrile at -30℃; for 0.0833333h; Glovebox; Stage #2: silver(I) trifluoromethoxide In acetonitrile at 20℃; for 12h; Glovebox;	95.8%

3,5-dimethoxybenzyl bromide (877-88-3) → 3,5,3',5'-tetramethoxy-bibenzyl (22976-41-6)

Conditions	Yield
With iodine; magnesium In diethyl ether for 2.5h; Heating;	95%
With (Cp2TiCl)2; water In tetrahydrofuran for 3h; Inert atmosphere;	90%
With sodium In diethyl ether for 20h; Heating;	68%

3,5-dimethoxybenzyl bromide (877-88-3) → 2-bromo-1-(bromomethyl)-3,5-dimethoxybenzene (34132-25-7)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 0℃; for 1h;	95%
With N-Bromosuccinimide In dichloromethane at 0℃; for 1h;	95%
With N-Bromosuccinimide In dichloromethane at 20℃; for 1h;	87%
With N-Bromosuccinimide In dichloromethane at 20℃; for 4h;	86%
With N-Bromosuccinimide In dichloromethane at 0℃; for 1h; Inert atmosphere;

2-Methylcyclopentanone (1120-72-5) + 3,5-dimethoxybenzyl bromide (877-88-3) → 2-(3,5-dimethoxybenzyl)-2-methylcyclopentanone

Conditions	Yield
Stage #1: 2-Methylcyclopentanone With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 6.5h; Stage #2: 3,5-dimethoxybenzyl bromide In tetrahydrofuran; hexane for 96h; Heating; Further stages.;	95%

3,5-dimethoxybenzyl bromide (877-88-3) + sodium benzenesulfonate (873-55-2) → 3,5-dimethoxybenzyl phenyl sulfone

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 2h;	95%

Upstream product

• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 192997-46-9 (3,5-dimethoxyphenyl)methyl methanesulfonate 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 77-78-1 dimethyl sulfate 
• 4179-19-5 1,3-dimethoxy-5-methylbenzene 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 1132-21-4 3,5-dimethoxybenzoic acid 

Downstream Products

• 41497-42-1 1-(3,5-Dimethoxyphenyl)-2-methylsulfonyl-octan-3-on 
• 22976-41-6 3,5,3',5'-tetramethoxy-bibenzyl 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 4179-19-5 1,3-dimethoxy-5-methylbenzene 
• 73569-69-4 1-methylmethoxy-3,5-dimethoxybenzene 
• 141045-28-5 1,3-bis<1-(3,5-dimethoxybenzyl)benzimidazolo-2-yl>benzene 
• 141045-27-4 2,6-bis<1-(3,5-dimethoxybenzyl)benzimidazol-2-yl>pyridine 
• 125877-13-6 trans-2-<(3,5-dimethoxyphenyl)methyl>-3--cyclopentan-1-one 
• 125846-92-6 trans-2-<(3,5-dimethoxyphenyl)methyl>-3--3,4,5,6-tetrahydropyran-2-one 
• 75887-69-3 1-<3,5-Dimethoxybenzyl>-aethan-1,1,2-tricarbonsaeure-triaethylester 
• 54879-37-7 N-(3,5-Dimethoxy-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzenesulfonamide 
• 96215-83-7 1,3-dimethoxyphenol-5-nonadecylbenzene 
• 82055-03-6 (1S,3aS,4S,7aS)-1-tert-Butoxy-4-<(1S)-2-(3,5-dimethoxyphenyl)-1-(phenylsulfonyl)ethyl>-5,5-(ethylendioxy)-2,3,3a,4,5,6,7,7a-octahydro-7a-methyl-1H-inden 
• 82079-97-8 (1S,3aS,4S,7aS)-1-tert-Butoxy-4-<(1R)-2-(3,5-dimethoxyphenyl)-1-(phenylsulfonyl)ethyl>-5,5-(ethylendioxy)-2,3,3a,4,5,6,7,7a-octahydro-7a-methyl-1H-inden 

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The invention provides a cyano-containing resveratrol analogue and a preparation method and application thereof, and relates to the field of medical compounds. A structure of the cyano-containing resveratrol analogue is shown in the formula of the description; 3,5-dihydroxy-benzoic acid is mainly used as a raw material, and the cyano-containing resveratrol analogue is prepared by the following steps of methylation, reduction, brominating, Abozove rearrangement, Wittig-Hornor reaction and Knoevenegal reaction; in the preparation process of the cyano-containing resveratrol analogue, the chemical substances with lower toxicity, such as trimethylsilyl cyanide and tetrabutylammonium fluoride, are used for replacing chemicals with higher toxicity, such as sodium cyanide or potassium cyanide, to introduce cyano, so that the damage to the health of an operator is greatly decreased, and the serious harm to environments is avoided. The preparation method has the advantages that the yield is higher, the environment-friendly effect is good, and multiple types of cyano-containing resveratrol analogue with anti-cancer activity on cells can be obtained.

Synthesis of trans-resveratrol using modified Julia olefination route

Bioactive hydroxystilbinoid-trans-resveratrol [(E)-3,5,4′ trihydroxy stilbene, 1] has been synthesized by modified Julia olefination method. The reaction between corresponding carbanion of benzothiazol-2-yl sulfone derivative and p-anisaldehyde dimethyl acetal with sodium hydride as a base, affords mainly cis-3,5,4′ trimethoxystilbene 10b with minor quantity of trans-isomev. Both the isomers have been separated in pure form and confirmed by their NMR spectral data. Demethylation of cis-3,5,4′ trimethoxystilbene either with AlCVpyridine or AlCl3/triethylamine results in the formation of trans-resveratrol.