5-bromo-6-methoxy-2,2-dimethyl-3-tosyloxy-3,4-dihydro-2H-naphtho[1,2-b]pyran

Base Information

• Chemical Name: 5-bromo-6-methoxy-2,2-dimethyl-3-tosyloxy-3,4-dihydro-2H-naphtho[1,2-b]pyran
• CAS No.: 909576-34-7
• Molecular Formula: C₂₃H₂₃BrO₅S
• Molecular Weight: 491.403
• Mol file: 909576-34-7.mol

Synonyms:

Chemical Property of 5-bromo-6-methoxy-2,2-dimethyl-3-tosyloxy-3,4-dihydro-2H-naphtho[1,2-b]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-bromo-6-methoxy-2,2-dimethyl-3-tosyloxy-3,4-dihydro-2H-naphtho[1,2-b]pyran

There total 7 articles about 5-bromo-6-methoxy-2,2-dimethyl-3-tosyloxy-3,4-dihydro-2H-naphtho[1,2-b]pyran 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:

[1,4]naphthoquinone (130-15-4) → 5-bromo-6-methoxy-2,2-dimethyl-3-tosyloxy-3,4-dihydro-2H-naphtho[1,2-b]pyran (909576-34-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 35 percent / AgNO₃; ammonium persulfate / acetonitrile; H₂O / 6 h / 65 - 70 °C

2.1: m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 20 °C

3.1: sodium dithionite / diethyl ether; H₂O / 0.5 h / 20 °C

3.2: 1.26 g / acetic acid; sulfuric acid / H₂O / 6 h / 20 °C

4.1: 90 percent / K₂CO₃ / acetone / 3 h / Heating

5.1: 95 percent / N-bromosuccinimide / CH₂Cl₂ / 0.17 h / 20 °C

6.1: pyridine / 16 h / 20 °C

With pyridine; ammonium persulfate; N-Bromosuccinimide; sodium dithionite; potassium carbonate; silver nitrate; 3-chloro-benzenecarboperoxoic acid; In diethyl ether; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/j.tet.2006.06.014

Reference yield:

2-(2,3-epoxy-3-methylbutyl)-1,4-naphthoquinone (909576-31-4) → 5-bromo-6-methoxy-2,2-dimethyl-3-tosyloxy-3,4-dihydro-2H-naphtho[1,2-b]pyran (909576-34-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium dithionite / diethyl ether; H₂O / 0.5 h / 20 °C

1.2: 1.26 g / acetic acid; sulfuric acid / H₂O / 6 h / 20 °C

2.1: 90 percent / K₂CO₃ / acetone / 3 h / Heating

3.1: 95 percent / N-bromosuccinimide / CH₂Cl₂ / 0.17 h / 20 °C

4.1: pyridine / 16 h / 20 °C

With pyridine; N-Bromosuccinimide; sodium dithionite; potassium carbonate; In diethyl ether; dichloromethane; water; acetone;

DOI:10.1016/j.tet.2006.06.014

Reference yield:

2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3,6-diol (909576-32-5) → 5-bromo-6-methoxy-2,2-dimethyl-3-tosyloxy-3,4-dihydro-2H-naphtho[1,2-b]pyran (909576-34-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / K₂CO₃ / acetone / 3 h / Heating

2: 95 percent / N-bromosuccinimide / CH₂Cl₂ / 0.17 h / 20 °C

3: pyridine / 16 h / 20 °C

With pyridine; N-Bromosuccinimide; potassium carbonate; In dichloromethane; acetone;

DOI:10.1016/j.tet.2006.06.014

upstream raw materials:

5-bromo-6-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol

p-toluenesulfonyl chloride

2-(2,3-epoxy-3-methylbutyl)-1,4-naphthoquinone

6-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol

Downstream raw materials:

lapachenole

mollugin

Refernces