{(E)-4-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-3-methyl-but-2-enyl}-triphenyl-phosphonium; bromide

Base Information

• Chemical Name: {(E)-4-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-3-methyl-but-2-enyl}-triphenyl-phosphonium; bromide
• CAS No.: 82599-03-9
• Molecular Formula: Br*C₃₃H₃₄ClNO₃P
• Molecular Weight: 638.969
• Mol file: 82599-03-9.mol

Synonyms:{(E)-4-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-3-methyl-but-2-enyl}-triphenyl-phosphonium; bromide

Chemical Property of {(E)-4-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-3-methyl-but-2-enyl}-triphenyl-phosphonium; bromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(E)-4-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-3-methyl-but-2-enyl}-triphenyl-phosphonium; bromide

There total 1 articles about {(E)-4-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-3-methyl-but-2-enyl}-triphenyl-phosphonium; 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: 74.0%

[5-((E)-4-Bromo-2-methyl-but-2-enyl)-2-chloro-3-methoxy-phenyl]-methyl-carbamic acid methyl ester (90605-50-8) + triphenylphosphine (603-35-0) → {(Z)-4-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-3-methyl-but-2-enyl}-triphenyl-phosphonium; bromide (91384-60-0) + {(E)-4-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-3-methyl-but-2-enyl}-triphenyl-phosphonium; bromide (82599-03-9)

Guidance literature:

In nitromethane; at 60 ℃; for 24h;

DOI:10.1021/jo00193a015

Reference yield:

{(E)-4-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-3-methyl-but-2-enyl}-triphenyl-phosphonium; bromide (82599-03-9) → {2-Chloro-3-methoxy-5-[(E)-2-methyl-4-(triphenyl-λ5-phosphanylidene)-but-2-enyl]-phenyl}-methyl-carbamic acid methyl ester (82599-04-0)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; N,N-dimethyl-formamide; pentane; 1. -78 deg C/30 min 2. -63 deg C/15 min;

DOI:10.1021/jo00193a015

Reference yield:

{(E)-4-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-3-methyl-but-2-enyl}-triphenyl-phosphonium; bromide (82599-03-9) → {(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-methanol (82599-08-4)

Guidance literature:

Multi-step reaction with 5 steps

1: tert-butyllithium / tetrahydrofuran; dimethylformamide; pentane / 1. -78 deg C/30 min 2. -63 deg C/15 min

2: 78 percent / tetrahydrofuran; dimethylformamide; pentane / 17 h

3: 1.46 g / acetic acid / tetrahydrofuran; H₂O / 48 h / -10 °C

4: 1. NaBH₄ 2. 12 N KOH / 1. CH₃OH, 0 deg C, 15 min 2. EtOH-H₂O, reflux, 22 h

5: 1. titanium tetraisopropoxide 2. tert-butyl hydroperoxide / 1. CH₂Cl₂, -20 deg C, 10 min 2. 1,2-dichlorethane, -20 deg C, 1.5 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium hydroxide; sodium tetrahydroborate; tert.-butyl lithium; acetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide; pentane;

DOI:10.1021/jo00193a015

upstream raw materials:

[5-((E)-4-Bromo-2-methyl-but-2-enyl)-2-chloro-3-methoxy-phenyl]-methyl-carbamic acid methyl ester

triphenylphosphine

Downstream raw materials:

{2-Chloro-3-methoxy-5-[(E)-2-methyl-4-(triphenyl-λ⁵-phosphanylidene)-but-2-enyl]-phenyl}-methyl-carbamic acid methyl ester

(2E,9E,11E)-(4S,5S,8R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-(4-chloro-3-methoxy-5-methylamino-phenyl)-7,7,8-trimethoxy-2,4,12-trimethyl-trideca-2,9,11-trien-1-ol

(2R,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxirane-2-carbaldehyde

{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-methanol