12-bromo-9α,10β-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene

Base Information

• Chemical Name: 12-bromo-9α,10β-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene
• CAS No.: 77061-16-6
• Molecular Formula: C₃₄H₂₃BrO₄
• Molecular Weight: 575.458
• Mol file: 77061-16-6.mol

Synonyms:12-bromo-9α,10β-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene

Chemical Property of 12-bromo-9α,10β-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 12-bromo-9α,10β-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene

There total 12 articles about 12-bromo-9α,10β-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene 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: 30.0%

trans-9,10-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene (77061-15-5) → 12-bromo-9α,10β-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene (77061-16-6)

Guidance literature:

With N-Bromosuccinimide; azobisisobutyronitrile; In tetrachloromethane; for 2h; Heating;

DOI:10.1021/jo00325a028

Reference yield:

7-methyl-6b,7,10,10a-tetrahydrofluoranthene (77096-72-1) → 12-bromo-9α,10β-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene (77061-16-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 80 percent / DDQ / xylene / 5 h / Heating

2: 80 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 3 h / Heating

3: 78 percent / diethyl ether / 30 h / Heating

4: 1.) diborane, 2.) 30percent H₂O₂ / 1.) THF, from 0 deg C to room temp., 8 h, 2.) reflux, 1 h

5: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

6: 85 percent / AgNO₃, 1.5 KOH / ethanol; H₂O / 2 h

7: SOCl₂ / benzene / 3 h / Heating

8: 1.) AlCl₃ / CS₂ / 1.) 0 deg C, 2.) reflux, 10 min

9: LiAlH₄ / tetrahydrofuran / 0.33 h / 20 °C

10: 60 percent / conc. H₂SO₄ / acetic acid / 3 h / 60 °C

11: 62 percent / 1.) I₂ / benzene / 1.) reflux, 2.) reflux, 2.5 h

12: 30 percent / N-bromsuccinimide, α,α'-azobis(isobutyronitrile) / CCl4 / 2 h / Heating

With potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; aluminium trichloride; thionyl chloride; Perbenzoic acid; sulfuric acid; azobisisobutyronitrile; dihydrogen peroxide; iodine; silver nitrate; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diborane; In tetrahydrofuran; carbon disulfide; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; acetic acid; xylene; benzene;

DOI:10.1021/jo00325a028

Reference yield:

7-methylfluoranthene (23339-05-1) → 12-bromo-9α,10β-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene (77061-16-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 80 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 3 h / Heating

2: 78 percent / diethyl ether / 30 h / Heating

3: 1.) diborane, 2.) 30percent H₂O₂ / 1.) THF, from 0 deg C to room temp., 8 h, 2.) reflux, 1 h

4: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

5: 85 percent / AgNO₃, 1.5 KOH / ethanol; H₂O / 2 h

6: SOCl₂ / benzene / 3 h / Heating

7: 1.) AlCl₃ / CS₂ / 1.) 0 deg C, 2.) reflux, 10 min

8: LiAlH₄ / tetrahydrofuran / 0.33 h / 20 °C

9: 60 percent / conc. H₂SO₄ / acetic acid / 3 h / 60 °C

10: 62 percent / 1.) I₂ / benzene / 1.) reflux, 2.) reflux, 2.5 h

11: 30 percent / N-bromsuccinimide, α,α'-azobis(isobutyronitrile) / CCl4 / 2 h / Heating

With potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; aluminium trichloride; thionyl chloride; Perbenzoic acid; sulfuric acid; azobisisobutyronitrile; dihydrogen peroxide; iodine; silver nitrate; pyridinium chlorochromate; diborane; In tetrahydrofuran; carbon disulfide; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; acetic acid; benzene;

DOI:10.1021/jo00325a028

upstream raw materials:

trans-9,10-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene

7-methyl-6b,7,10,10a-tetrahydrofluoranthene

7-methylfluoranthene

4-(7-fluoranthenyl)-1-butene

Downstream raw materials:

trans-9,10-dihydro-9,10-dihydroxybenzofluoranthene

trans-9,10-bis(benzoyloxy)-9,10-dihydrobenzofluoranthene

Refernces