Ethyl 3-(bromomethyl)phenoxyacetate

Base Information

• Chemical Name: Ethyl 3-(bromomethyl)phenoxyacetate
• CAS No.: 74232-79-4
• Molecular Formula: C11H13 Br O3
• Molecular Weight: 273.126
• DSSTox Substance ID: DTXSID20466624
• Wikidata: Q82293217
• Mol file: 74232-79-4.mol

Synonyms:74232-79-4;ethyl 3-(bromomethyl)phenoxyacetate;Ethyl 2-[3-(bromomethyl)phenoxy]acetate;Acetic acid,2-[3-(bromomethyl)phenoxy]-, ethyl ester;ETHYL 3-BROMOMETHYLPHENOXYACETATE;3-bromomethyl-1-ethoxycarbonylmethoxybenzene;SCHEMBL5563172;DTXSID20466624;FGQCYQBPCJMPCS-UHFFFAOYSA-N;ethyl 3 (bromomethyl)phenoxyacetate;AKOS030255505

Chemical Property of Ethyl 3-(bromomethyl)phenoxyacetate

Chemical Property:

• PSA: 35.53000
• LogP: 2.52340
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 272.00481
• Heavy Atom Count: 15
• Complexity: 196

Purity/Quality:

97% ^*data from raw suppliers

3-BROMOMETHYLPHENOXYACETIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)COC1=CC=CC(=C1)CBr

Technology Process of Ethyl 3-(bromomethyl)phenoxyacetate

There total 2 articles about Ethyl 3-(bromomethyl)phenoxyacetate 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:

3-hydroxymethyl-1-ethoxycarbonylmethoxybenzene (93306-78-6) → 3-bromomethyl-1-ethoxycarbonylmethoxybenzene (74232-79-4)

Guidance literature:

With boron tribromide; In dichloromethane; ethyl acetate;

Reference yield:

3-Hydroxybenzyl alcohol (620-24-6) → 3-bromomethyl-1-ethoxycarbonylmethoxybenzene (74232-79-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / acetone / 12 h / Reflux

2: triphenylphosphine; N-Bromosuccinimide / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With N-Bromosuccinimide; potassium carbonate; triphenylphosphine; In tetrahydrofuran; acetone;

DOI:10.1002/cmdc.201300316

Reference yield: 95.0%

3-bromomethyl-1-ethoxycarbonylmethoxybenzene (74232-79-4) + (2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidine (187993-59-5) → (2R)-2-(4,5-diphenyloxazol-2-yl)-1-(3-ethoxycarbonylmethoxybenzyl)pyrrolidine (187992-65-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.06.076

upstream raw materials:

3-hydroxymethyl-1-ethoxycarbonylmethoxybenzene

3-Hydroxybenzyl alcohol

Downstream raw materials:

(2S)-2-(4,5-diphenyloxazol-2-yl)-1-(3-ethoxycarbonylmethoxybenzyl)pyrrolidine

(2R)-2-(4,5-diphenyloxazol-2-yl)-1-(3-ethoxycarbonylmethoxybenzyl)pyrrolidine

ethyl 3-{[(2R,4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidin-1-yl]methyl}phenoxyacetate

Refernces

• 1、 Ding, Xiao,Li, Yan,Lv, Li,Zhou, Mi,Han, Li,Zhang, Zhengxi,Ba, Qian,Li, Jingquan,Wang, Hui,Liu, Hong,Wang, Renxiao. "De novo design, synthesis and evaluation of benzylpiperazine derivatives as highly selective binders of Mcl-1". . p. 1986 - 2014. Retrieved 2014/01/06.
• 2、 -. "4,5-diaryl oxazole derivatives". . . Retrieved 2008/06/13.