(R)-(+)-t-butyl(phenyl)phosphinic bromide

Base Information

• Chemical Name: (R)-(+)-t-butyl(phenyl)phosphinic bromide
• CAS No.: 128014-10-8
• Molecular Formula: C₁₀H₁₄BrOP
• Molecular Weight: 261.098
• Mol file: 128014-10-8.mol

Synonyms:(R)-(+)-t-butyl(phenyl)phosphinic bromide

Chemical Property of (R)-(+)-t-butyl(phenyl)phosphinic bromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(+)-t-butyl(phenyl)phosphinic bromide

There total 26 articles about (R)-(+)-t-butyl(phenyl)phosphinic bromide 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: 95.0%

(S)-(-)-t-butyl(phenyl)phosphine oxide (6057-79-0,57956-51-1,82945-11-7) → (R)-(+)-t-butyl(phenyl)phosphinic bromide (128014-10-8)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; at 0 ℃;

DOI:10.1002/chem.19970031221

Reference yield:

diethyl (3-methylbenzyl) phosphate (7145-06-4) → (R)-(+)-t-butyl(phenyl)phosphinic bromide (128014-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; rubidium carbonate; C₃₆H₄₄NOPS / acetonitrile / 40 h / 55 °C / Sealed tube; Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Sealed tube; Inert atmosphere

2.2: 1 h / 0 - 20 °C / Sealed tube; Inert atmosphere

With rubidium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; C₃₆H₄₄NOPS; sodium hydride; In tetrahydrofuran; acetonitrile;

DOI:10.1002/anie.202111957

Reference yield:

m-(trifluoromethyl)benzyl diethyl phosphate (128732-38-7) → (R)-(+)-t-butyl(phenyl)phosphinic bromide (128014-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; rubidium carbonate; C₃₆H₄₄NOPS / acetonitrile / 14 h / 55 °C / Sealed tube; Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Sealed tube; Inert atmosphere

2.2: 1 h / 0 - 20 °C / Sealed tube; Inert atmosphere

With rubidium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; C₃₆H₄₄NOPS; sodium hydride; In tetrahydrofuran; acetonitrile;

DOI:10.1002/anie.202111957

upstream raw materials:

(R)-(+)-S-methyl tert-butylphenylphosphinothiolate

(S)-(-)-t-butyl(phenyl)phosphine oxide

(S)-(-)-S-methyl tert-butylphenylphosphinothiolate

(R_p)-(+)-tert-Butylphenylphosphinothioic acid

Downstream raw materials:

C₁₇H₂₂NOP

(-)-(S)-tert-butylphenylphosphinobromidothionate

P(S)S_P(O)>-(-)-bis(t-butylphenyl)thiophosphinate

Refernces

• 1、 Francesco, Irene Notar,Wagner, Alain,Colobert, Francoise. "Stereoselective addition of Grignard reagents to new P-chirogenic N-phosphinoylimines". scheme or table. p. 2139 - 2141. Retrieved 2010/07/04.
• 2、 Omelanczuk, Jan,Mikolajczyk, Marian. "Unexpected Opposite Stereochemistries and Different Mechanisms of Nucleophilic Substitution Reactions of Homochiral tert-Butylphenylthiophosphinoyl Chloride and Bromide". . p. 2223 - 2224. Retrieved 2007/10/02.