cis-1-(3,4-dimethoxyphenyl)-3,5,6-trimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide

Base Information

• Chemical Name: cis-1-(3,4-dimethoxyphenyl)-3,5,6-trimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide
• CAS No.: 103477-62-9
• Molecular Formula: C₁₉H₂₂O₇S
• Molecular Weight: 394.445
• Mol file: 103477-62-9.mol

Synonyms:cis-1-(3,4-dimethoxyphenyl)-3,5,6-trimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide

Chemical Property of cis-1-(3,4-dimethoxyphenyl)-3,5,6-trimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-1-(3,4-dimethoxyphenyl)-3,5,6-trimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide

There total 8 articles about cis-1-(3,4-dimethoxyphenyl)-3,5,6-trimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide 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:

3,4-dimethoxy-benzaldehyde (120-14-9) → cis-1-(3,4-dimethoxyphenyl)-3,5,6-trimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide (103477-62-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / Br₂, CH₃COOH / 5 h / Ambient temperature

2: 98 percent / p-toluenosulfonic acid / benzene / 2 h / Heating

3: 1.) tetramethylene diamine, n-butyllithium, (n-Bu)3P*CuI / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, from -78 deg C to RT, 0.5 h

4: 95 percent / 10percent aq. HCl / diethyl ether / 2 h / Ambient temperature

5: 67 percent / SO₂ / thiophene / 8 h / Irradiation

6: p-toluenosulfonic acid / CH₂Cl₂ / 1 h / Heating

With hydrogenchloride; n-butyllithium; CuI*P(n-Bu)3; N,N,N,N,-tetramethylethylenediamine; sulfur dioxide; bromine; toluene-4-sulfonic acid; acetic acid; In thiophene; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo00368a018

Reference yield:

4-bromomethyl-1,2-dimethoxybenzene (21852-32-4) → cis-1-(3,4-dimethoxyphenyl)-3,5,6-trimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide (103477-62-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) tetramethylene diamine, n-butyllithium, (n-Bu)3P*CuI / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, from -78 deg C to RT, 0.5 h

2: 95 percent / 10percent aq. HCl / diethyl ether / 2 h / Ambient temperature

3: 67 percent / SO₂ / thiophene / 8 h / Irradiation

4: p-toluenosulfonic acid / CH₂Cl₂ / 1 h / Heating

With hydrogenchloride; n-butyllithium; CuI*P(n-Bu)3; N,N,N,N,-tetramethylethylenediamine; sulfur dioxide; toluene-4-sulfonic acid; In thiophene; diethyl ether; dichloromethane;

DOI:10.1021/jo00368a018

Reference yield:

2-bromo-4,5-dimethoxybenzaldehyde (5392-10-9) → cis-1-(3,4-dimethoxyphenyl)-3,5,6-trimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide (103477-62-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / p-toluenosulfonic acid / benzene / 2 h / Heating

2: 1.) tetramethylene diamine, n-butyllithium, (n-Bu)3P*CuI / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, from -78 deg C to RT, 0.5 h

3: 95 percent / 10percent aq. HCl / diethyl ether / 2 h / Ambient temperature

4: 67 percent / SO₂ / thiophene / 8 h / Irradiation

5: p-toluenosulfonic acid / CH₂Cl₂ / 1 h / Heating

With hydrogenchloride; n-butyllithium; CuI*P(n-Bu)3; N,N,N,N,-tetramethylethylenediamine; sulfur dioxide; toluene-4-sulfonic acid; In thiophene; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo00368a018

upstream raw materials:

methanol

1-(3,4-dimethoxyphenyl)-3-hydroxy-5,6-dimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide

4-bromomethyl-1,2-dimethoxybenzene

2-bromo-4,5-dimethoxybenzaldehyde

Downstream raw materials:

(1S,2R,3S,4S)-1-(3,4-Dimethoxy-phenyl)-4,6,7-trimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester

r-1-(3,4-dimethoxyphenyl)-t-2,c-3-bis(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene

dimethyl trans(1,2),trans(2,3)-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-1,3,4-tetrahydronaphthalene-2,3-dicarboxylate

dimethyl trans-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-1,2-dihydronaphthalene-2,3-dicarboxylate