tert-butyl 2-fluoro-4-hydroxyphenylcarbamate

Base Information

• Chemical Name: tert-butyl 2-fluoro-4-hydroxyphenylcarbamate
• CAS No.: 911297-02-4
• Molecular Formula: C₁₁H₁₄FNO₃
• Molecular Weight: 227.235
• Mol file: 911297-02-4.mol

Synonyms:N-(2-fluoro-4-hydroxyphenyl)carbamic acid tert-butyl ester

Chemical Property of tert-butyl 2-fluoro-4-hydroxyphenylcarbamate

Chemical Property:

• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99.99%HPLC ^*data from raw suppliers

4-(Boc-amino)-3-fluoro-phenol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-fluoro-4-hydroxyphenylcarbamate

There total 2 articles about tert-butyl 2-fluoro-4-hydroxyphenylcarbamate 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: 90.0%

di-tert-butyl dicarbonate (24424-99-5) + 4-amino-3-fluorophenol (399-95-1) → N-(2-fluoro-4-hydroxyphenyl)carbamic acid tert-butyl ester (911297-02-4)

Guidance literature:

With indium(III) chloride; at 35 ℃; for 2h;

DOI:10.1021/jm900242c

Reference yield:

3-fluoro-4-nitrophenol (394-41-2) → N-(2-fluoro-4-hydroxyphenyl)carbamic acid tert-butyl ester (911297-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd-C

2: 27 percent / Et₃N / tetrahydrofuran

With hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/j.bmc.2006.06.019

Reference yield: 98.0%

N-(2-fluoro-4-hydroxyphenyl)carbamic acid tert-butyl ester (911297-02-4) + 4-chloro-3-nitro-2-pyridinamine (6980-08-1) → 4-(4-N-(tert-butoxycarbonyl)amino-3-fluorophenoxy)-3-nitro-2-aminopyridine (1163720-60-2)

Guidance literature:

N-(2-fluoro-4-hydroxyphenyl)carbamic acid tert-butyl ester; With sodium hydride; In dimethyl sulfoxide; mineral oil; at 20 ℃; for 0.25h; Inert atmosphere;

4-chloro-3-nitro-2-pyridinamine; In dimethyl sulfoxide; mineral oil; at 110 ℃; for 1h;

upstream raw materials:

di-tert-butyl dicarbonate

4-amino-3-fluorophenol

3-fluoro-4-nitrophenol

Downstream raw materials:

(S)-{4-[2-(4-cyano-3-trifluoromethylphenylcarbamoyl)-2-hydroxypropoxy]-2-fluorophenyl}carbamic acid tert-butyl ester

(S)-{2-fluoro-4-[2-hydroxy-2-(4-nitro-3-trifluoromethylphenylcarbamoyl)propoxy]phenyl}carbamic acid tert-butyl ester

(S)-3-(4-amino-3-fluorophenoxy)-2-hydroxy-2-methyl-N-(4-cyano-3-trifluoromethylphenylcarbamoyl)propionamide

3-(4-amino-3-fluoro-phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide

Refernces

• 1、 -. "Preparation method of regrafenib derivatives". Paragraph 0054; 0081. . Retrieved 2018/10/19.
• 2、 Ménard, Delphine,Niculescu-Duvaz, Ion,Dijkstra, Harmen P.,Niculescu-Duvaz, Dan,Suijkerbuijk, Bart M. J. M.,Zambon, Alfonso,Nourry, Arnaud,Roman, Esteban,Davies, Lawrence,Manne, Helen A.,Friedlos, Frank,Kirk, Ruth,Whittaker, Steven,Gill, Adrian,Taylor, Richard D.,Marais, Richard,Springer, Caroline J.. "Novel potent BRAF inhibitors: Toward 1 nM compounds through optimization of the central phenyl ring". supporting information; experimental part. p. 3881 - 3891. Retrieved 2010/02/17.