83333-66-8

Upstream product

• 140-67-0 Estragole 
• 37983-33-8 1-(1,3-dibromopropan-2-yl)-4-methoxybenzene 

Downstream Products

• 860764-10-9 2-(4-methoxy-phenyl)-prop-1-en-1-ol 
• 67168-96-1 1,3-dichloro-2-(4-methoxyphenyl)propane 
• 67168-94-9 1,2-dichloro-3-(4-methoxyphenyl)propane 
• 83333-69-1 1-bromo-3-chloro-2-(4-methoxyphenyl)propane 
• 83333-67-9 1-bromo-2-chloro-3-(4-methoxyphenyl)propane 
• 83333-68-0 2-bromo-1-chloro-3-(4-methoxyphenyl)propane 
• 37983-33-8 1-(1,3-dibromopropan-2-yl)-4-methoxybenzene 
• 252058-33-6 2-(4-methoxyphenyl)propanal 
• 140-67-0 Estragole 

Relevant academic research and scientific papers

A Highly Efficient Method for the Bromination of Alkenes, Alkynes and Ketones Using Dimethyl Sulfoxide and Oxalyl Bromide

The pairing of DMSO and oxalyl bromide is reported as a highly efficient brominating reagent for various alkenes, alkynes and ketones. This bromination approach demonstrates remarkable advantages, such as mild conditions, low cost, short reaction times, provides excellent yields in most cases and represents a very attractive alternative for the preparation of dibromides and α-bromoketones.

Dibromination of alkenes with LiBr and H2O2 under mild conditions

Electron-rich and electron-poor alkenes, and alkenes bearing protecting groups can be efficiently and stereoselectively converted to trans-dibromides using LiBr/H2O2 and AcOH as a proton source in 1,4-dioxane. For most substrates addition of 0.1 mol% of PhTeTePh enhances the reaction rate and the yield of the products. Experimental data suggest that the brominating agent prepared in situ is molecular bromine and that LiBr assists the activation of H2O2 allowing bromination to occur using AcOH as a mild proton source in uncatalyzed experiments. Scale-up is feasible: 10.0 mmol of 1-octene was quantitatively converted to 1,2-dibromooctene in one hour of reaction at room temperature.

Bromination of olefins with HBr and DMSO

A simple and inexpensive methodology is reported for the conversion of alkenes to 1,2-dibromo alkanes via oxidative bromination using HBr paired with dimethyl sulfoxide, which serves as the oxidant as well as cosolvent. The substrate scope includes 21 olefins brominated in good to excellent yields. Three of six styrene derivatives yielded bromohydrins under the reaction conditions.

Electrophilic bromination of alkenes, alkynes, and aromatic amines with iodic acid/potassium bromide under mild conditions

Bromination of alkenes, alkynes, and aromatic amines has efficiently been carried out at room temperature in short reaction times using HIO 3/KBr in CH2Cl2/H2O (1:1) to prepare corresponding brominated compounds in excellent yields.

Elctrophilic bromination of alkenes, alkynes, and aromatic amines with potassium bromide/orthoperiodic acid under mild conditions

Bromination of alkenes, alkynes, and aromatic amines has efficiently been carried out at room temperature in short reaction times using potassium bromide/orthoperiodic acid in dichloromethane-water (1:1) to prepare the corresponding bromo compounds with excellent yields.

Chavicol formation in sweet basil (Ocimum basilicum): Cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction

Propenyl- and allyl-phenols, such as methylchavicol, p-anol and eugenol, have gained importance as flavoring agents and also as putative precursors in the biosynthesis of 9,9′-deoxygenated lignans, many of which have potential medicinal applications. In spite of several decades of investigation, however, the complete biosynthetic pathway to a propenyl/allylphenol had not yet been reported. We have subjected a Thai basil variety accumulating relatively large amounts of the simplest volatile allylphenol, methylchavicol, to in vivo administration of radiolabeled precursors and assays of protein preparations in vitro. Through these experiments, the biosynthesis of chavicol was shown to occur via the phenylpropanoid pathway to p-coumaryl alcohol. Various possibilities leading to deoxygenation of the latter were examined, including reduction of the side-chain double bond to form p-dihydrocoumaryl alcohol, followed by dehydration to afford chavicol, as well as formation of p-methoxycinnamyl alcohol, with further side-chain modification to afford methylchavicol. A third possibility studied was activation of the side-chain alcohol of p-coumaryl alcohol, e.g. via esterification, to form a more facile leaving group via reductive elimination. The latter was shown to be the case using p-coumaryl esters as potential substrates for a NAD(P)H-dependent reductase to afford chavicol, which is then O-methylated to afford methylchavicol. The Royal Society of Chemistry 2006.

Direct transformation of 1,3-dihalides into dithianes and dithiepines via a novel one-pot reaction with carbon disulfide and sodium borohydride

1,3-Dithianes and -dithiepines are prepared via an experimentally simple and efficient direct transformation of 1,n-alkyl dihalides utilizing carbon disulfide and sodium borohydride.

Unusual Secondary to Primary System Rearrangement via Ring Opening of 1-(3-Halopropylene)-4-methoxybenzenium Ions

The effect of electron-withdrawing groups on the ring opening of benzenium ions has been investigated by kinetics, equilibrium studies, and product analysis.The use of SnX4 (X = Br or Cl) compounds as highly ionizing solvents and as conveying agents of the X- nucleophile works quite well. 1,2-Dihalo-3-(4-methoxyphenyl)propanes (2; X = Br or Cl) and 1,3-dihalo-2-(4-methoxyphenyl)propanes (3; X = Br or Cl) equilibrate at 100 deg C in SnX'4 (X' = Br or Cl) when X = X'; they undergo halogen exchange with partial rearrangement (2 -> 3 and 3 -> 2) when X differs from X'.This 2 -> 3 rearrangement is very unusual in benzenium ion chemistry and yields primary halide products.For X = X', the 3 to 2 equilibrium constant K is 10.1, whatever the halogen; the forward rate constants K32 are 1.82x10-5 and 1.86x10-4 s-1 for X = Br and Cl, respectively.For X different from X' (X = Br, X' = Cl), as well as for mixed compounds containing both halogens, the relative proportions of rearranged and unrearranged products have been examined in terms of the evolving reactions.Results indicate a mechanism involving 1-(3-halopropylene)-4-methoxybenzenium ions which, when they react with solvated halide ions, yield a mixture of 1,2- and 1,3-dihalides in equal amounts.This absence of ring-opening regioselectivity which contrasts with that of usual unsubstituted propylenebenzenium ions is attributed mainly to the electron-withdrawing effect of the halogen. Benzenium ion involvement in nucleophilic substitution can bring about significant rearrangement in secondary compounds containing electron-withdrawing groups.