(S)-1-(4-BENZYLOXY-3-NITRO-PHENYL)-2-BROMO-ETHANOL

Base Information

• Chemical Name: (S)-1-(4-BENZYLOXY-3-NITRO-PHENYL)-2-BROMO-ETHANOL
• CAS No.: 193761-53-4
• Molecular Formula: C15H14 Br N O4
• Molecular Weight: 352.184
• Mol file: 193761-53-4.mol

Synonyms:Benzenemethanol,a-(bromomethyl)-3-nitro-4-(phenylmethoxy)-,(S)-

Chemical Property of (S)-1-(4-BENZYLOXY-3-NITRO-PHENYL)-2-BROMO-ETHANOL

Chemical Property:

• Refractive Index: 1.638
• Boiling Point: 493.9±45.0 °C(Predicted)
• PKA: 12.21±0.20(Predicted)
• PSA: 75.28000
• Density: 1.529±0.06 g/cm3(Predicted)
• LogP: 4.12530
• Storage Temp.: 2-8°C

Purity/Quality:

98.5% ^*data from raw suppliers

(S)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate in synthesis of (R,R)-Formoterol.

Technology Process of (S)-1-(4-BENZYLOXY-3-NITRO-PHENYL)-2-BROMO-ETHANOL

There total 6 articles about (S)-1-(4-BENZYLOXY-3-NITRO-PHENYL)-2-BROMO-ETHANOL 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: 98.0%

4-benzyloxy-3-nitrophenacyl bromide (43229-01-2) → (S)-1-(4-(benzyloxy)-3-nitrophenyl)-2-bromoethanol (193761-53-4)

Guidance literature:

With oxazaborolidine from cis (1S,2R)-aminoindanol and trimethylboroxine; borane; In tetrahydrofuran; at -15 ℃;

DOI:10.1016/S0040-4039(97)00088-9

Reference yield: 7.0%

4-benzyloxy-3-nitrophenacyl bromide (43229-01-2) → (S)-4-benzyloxy-3-nitrostyrene oxide (188730-96-3) + (S)-1-(4-(benzyloxy)-3-nitrophenyl)-2-bromoethanol (193761-53-4) + (R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol (188690-82-6)

Guidance literature:

With sodium formate; Triton X-100; (R,R)-TsDPEN; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; In water; at 28 ℃; for 6h; Title compound not separated from byproducts;

DOI:10.1021/jo0514826

Reference yield:

4-benzyloxy-3-nitrophenacyl bromide (43229-01-2) → (S)-1-(4-(benzyloxy)-3-nitrophenyl)-2-bromoethanol (193761-53-4) + (R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol (188690-82-6)

Guidance literature:

With boron trifluoride-tetrahydrofuran complex; (-)-(1R,2S)-1-amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene; In tetrahydrofuran; at 0 ℃; for 2h; Product distribution; other reag., other temp.;

DOI:10.1016/S0040-4039(98)00137-3

upstream raw materials:

4-benzyloxy-3-nitrophenacyl bromide

4'-hydroxy-3'-nitroacetophenone

4-benzyloxy-3-nitroacetophenone

benzyl chloride

Downstream raw materials:

N-(5-(2-((2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)butyl)amino)-1-hydroxyethyl)-2-hydroxyphenyl)formamide

N-(2-(benzyloxy)-5-((S)-2-bromo-1-hydroxyethyl)phenyl)formamide

(1S)-1-(3-amino-4-benzyloxyphenyl)-2-bromoethan-1-ol

(S)-1-(3-Amino-4-benzyloxy-phenyl)-2-{benzyl-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethyl]-amino}-ethanol

Refernces

• 1、 Mahale, Rajendra D.,Chaskar, Sudhir P.,Patil, Kiran E.,Maikap, Golak C.,Gurjar, Mukund K.. "Corey-itsuno reduction of ketones: A development of safe and inexpensive process for synthesis of some API intermediates". supporting information; experimental part. p. 710 - 713. Retrieved 2012/07/27.
• 2、 -. "ACETAMIDE STEREOISOMER". Page/Page column 4. . Retrieved 2009/04/24.