5463-71-8

Usage

Uses

Used in Pharmaceutical Synthesis:
Bromosaffrole is used as a precursor in the synthesis of various pharmaceuticals, primarily for the production of amphetamines and other psychoactive substances. Its chemical properties make it a valuable component in the creation of these compounds.
Used in Chemical Research:
Due to its unique chemical structure and properties, Bromosaffrole is also utilized in chemical research for the development of new compounds and understanding of chemical reactions involving safrole derivatives.

InChI:InChI=1/C10H11BrO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6H2,1H3

Synthetic route

diethyl 4-(1-(benzo[d][1,3]dioxol-5-yl)propan-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate → 3-<3,4-(methylenedioxy)-phenyl>-2-bromopropane (5463-71-8)

Conditions	Yield
With dipotassium peroxodisulfate; tris(2,2′-bipyridyl)dichlororuthenium(II) hexahydrate; sodium bromide In water; acetonitrile at 20℃; for 24h; Sealed tube; Inert atmosphere; Irradiation; regioselective reaction;	94%

1-allyl-3,4-methylenedioxybenzene (94-59-7) → 3-<3,4-(methylenedioxy)-phenyl>-2-bromopropane (5463-71-8)

Conditions	Yield
With water; hydrogen bromide

1-allyl-3,4-methylenedioxybenzene (94-59-7) → 3-<3,4-(methylenedioxy)-phenyl>-2-bromopropane (5463-71-8) + 3-<3,4-(methylenedioxy)phenyl>-1-bromopropane (28437-31-2)

Conditions	Yield
With borane; bromine 1.) 0 deg C, 1 h, THF, 2.) 0 deg C, 30 min, THF, H2O; Yield given. Multistep reaction. Yields of byproduct given;

3-<3,4-(methylenedioxy)-phenyl>-2-bromopropane (5463-71-8) → 1-(1,3-benzodioxol-5-yl)-2-propanone (4676-39-5)

Conditions	Yield
With potassium hydroxide; 2-nitropropane

3-<3,4-(methylenedioxy)-phenyl>-2-bromopropane (5463-71-8) + (3,4,5-trimethoxyphenyl)acetone (16603-18-2) → erythro-2,3-dimethyl-4-(3,4-methylenedioxyphenyl)-1-(3,4,5-trimethoxyphenyl)-2-butanol + threo-2,3-dimethyl-4-(3,4-methylenedioxyphenyl)-1-(3,4,5-trimethoxyphenyl)-2-butanol

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide 1.) THF, HMPA, 5 min, 2.) THF, HMPA, 25 deg C, 40 min;
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide 1.) THF, HMPA, 5 min, 2.) THF, HMPA, 25 deg C, 40 min; Yield given. Yields of byproduct given;

Upstream product

• 94-59-7 1-allyl-3,4-methylenedioxybenzene 

Downstream Products

• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 

Relevant academic research and scientific papers

Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation

An unprecedented deformylative halogenation of aldehydes to alkyl halides is presented. Under oxidative conditions, 1,4-dihydropyridine (DHP), derived from an aldehyde, generated a C(sp3)- radical that coupled with a halogen radical that was generated from inexpensive and atom-economical halogen sources (NaBr, NaI, or HCl), to yield an alkyl halide. Because of the mild conditions, a wide range of functional groups were tolerated, and excellent site selectivity was achieved.

Facile Conversion of Alkenes into Alkyl Bromides via Reaction of Organoboranes with Bromine or Bromine Chloride

Organoboranes react with either bromine or bromine chloride in aqueous media to yield the corresponding alkyl bromides under surprisingly mild conditions.The reaction is ideal for the synthesis of functionally substituted organic bromides.Sodium bromide may be utilized as the bromine source via its in situ conversion to bromine chloride by using mild oxidizing agents.