Methyl 2-(2-bromo-5-methoxyphenyl)acetate

Base Information

• Chemical Name: Methyl 2-(2-bromo-5-methoxyphenyl)acetate
• CAS No.: 117565-90-9
• Molecular Formula: C10H11BrO3
• Molecular Weight: 259.1
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID60443171
• Nikkaji Number: J2.659.377H
• Mol file: 117565-90-9.mol

Synonyms:METHYL 2-(2-BROMO-5-METHOXYPHENYL)ACETATE;117565-90-9;Benzeneacetic acid, 2-bromo-5-methoxy-, methyl ester;Methyl 2-(2-bromo-5-methoxy-phenyl)acetate;2-Bromo-5-methoxy-benzeneacetic acid methyl ester;SCHEMBL898733;DTXSID60443171;IGZZCVJQEPJTNK-UHFFFAOYSA-N;AKOS015909207;Methyl (2-bromo-5-methoxyphenyl)acetate;2-Bromo-5-methoxybenzeneacetic acid methyl ester;(2-Bromo-5-methoxyphenyl)acetic acid methyl ester;A803783;METHYL2-(2-BROMO-5-METHOXYPHENYL)ACETATE;(2-Bromo-5-methoxy-phenyl)-acetic acid methyl ester

Chemical Property of Methyl 2-(2-bromo-5-methoxyphenyl)acetate

Chemical Property:

• Boiling Point: 309.006 °C at 760 mmHg
• Flash Point: 140.682 °C
• PSA: 35.53000
• Density: 1.42 g/cm³
• LogP: 2.17320
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 257.98916
• Heavy Atom Count: 14
• Complexity: 196

Purity/Quality:

98%min ^*data from raw suppliers

METHYL2-(2-BROMO-5-METHOXYPHENYL)ACETATE ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)Br)CC(=O)OC

Technology Process of Methyl 2-(2-bromo-5-methoxyphenyl)acetate

There total 5 articles about Methyl 2-(2-bromo-5-methoxyphenyl)acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

methanol (67-56-1) + 2-(2-bromo-5-methoxyphenyl)acetic acid (86826-93-9) → methyl 2-(2'-bromo-5'-methoxyphenyl)acetate (117565-90-9)

Guidance literature:

With sulfuric acid; for 0.5h; Reflux;

DOI:10.1016/j.tet.2013.07.095

Reference yield:

m-methoxyphenylacetic acid (1798-09-0) → methyl 2-(2'-bromo-5'-methoxyphenyl)acetate (117565-90-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Br₂ / CH₂Cl₂ / 2 h / 20 °C

2: SOCl₂ / 4 h / Heating

With thionyl chloride; bromine; In dichloromethane;

DOI:10.1021/ja0602997

Reference yield:

2-bromo-5-methoxybenzyl bromide (19614-12-1) → methyl 2-(2'-bromo-5'-methoxyphenyl)acetate (117565-90-9)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethylsulfoxide / 0.75 h / Ambient temperature

2: aq. KOH / ethanol / 14 h / Heating

3: conc. H₂SO₄ / 7 h / Heating

With potassium hydroxide; sulfuric acid; In ethanol; dimethyl sulfoxide;

upstream raw materials:

methanol

2-(2-bromo-5-methoxyphenyl)acetic acid

m-methoxyphenylacetic acid

4-bromo-3-methylanisole

Downstream raw materials:

methyl 2-(2-bromo-5-methoxyphenyl)-2-methylpropanoate

methyl 2-(2-bromo-5-methoxyphenyl)-2-formylacetate

methyl 2-(2'-bromo-5'-methoxyphenyl)hexanoate

methyl 2-(5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate

Refernces

• 1、 Mori, Keiji,Isogai, Ryo,Kamei, Yuto,Yamanaka, Masahiro,Akiyama, Takahiko. "Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp3)-H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process". supporting information. p. 6203 - 6207. Retrieved 2018/05/23.
• 2、 Momoi, Yuichi,Okuyama, Kei-Ichiro,Toya, Hiroki,Sugimoto, Kenji,Okano, Kentaro,Tokuyama, Hidetoshi. "Total synthesis of (-)-Haouamine B pentaacetate and structural revision of haouamine B". supporting information. p. 13215 - 13219. Retrieved 2015/01/09.