phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-2-yl)methanone

Base Information

• Chemical Name: phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-2-yl)methanone
• CAS No.: 1344109-66-5
• Molecular Formula: C₁₈H₁₄BNO₃
• Molecular Weight: 303.125
• Mol file: 1344109-66-5.mol

Synonyms:phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-2-yl)methanone

Chemical Property of phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-2-yl)methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-2-yl)methanone

There total 9 articles about phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-2-yl)methanone 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: 23.0%

6-(pyrrol-1-yl)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (1344109-52-9) + benzoyl chloride (98-88-4) → phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-2-yl)methanone (1344109-66-5) + phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-3-yl)methanone (1344109-55-2)

Guidance literature:

With tin(IV) chloride; In dichloromethane;

DOI:10.1016/j.cclet.2011.06.005

Reference yield:

2-bromo-4-nitrotoluene (7745-93-9) → phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-2-yl)methanone (1344109-66-5) + phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-3-yl)methanone (1344109-55-2)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine; potassium permanganate / water / 12 h / Reflux

2: thionyl chloride / 6 h / Reflux

3: triethylamine / 1 h

4: tin(II) chloride dihdyrate / ethyl acetate / 1 h / Reflux

5: acetic acid / 0.5 h / Reflux

6: lithium borohydride / methanol / 12 h / 0 °C

7: n-butyllithium; Triisopropyl borate / tetrahydrofuran / 12 h / -80 °C

8: tin(IV) chloride / dichloromethane

With pyridine; potassium permanganate; lithium borohydride; n-butyllithium; thionyl chloride; tin(II) chloride dihdyrate; Triisopropyl borate; tin(IV) chloride; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; 5: Paal-Knorr pyrrole synthesis / 8: Friedel Crafts acylation;

DOI:10.1016/j.cclet.2011.06.005

Reference yield:

2-bromo-4-nitrobenzoic acid (16426-64-5) → phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-2-yl)methanone (1344109-66-5) + phenyl(1-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)pyrrol-3-yl)methanone (1344109-55-2)

Guidance literature:

Multi-step reaction with 7 steps

1: thionyl chloride / 6 h / Reflux

2: triethylamine / 1 h

3: tin(II) chloride dihdyrate / ethyl acetate / 1 h / Reflux

4: acetic acid / 0.5 h / Reflux

5: lithium borohydride / methanol / 12 h / 0 °C

6: n-butyllithium; Triisopropyl borate / tetrahydrofuran / 12 h / -80 °C

7: tin(IV) chloride / dichloromethane

With lithium borohydride; n-butyllithium; thionyl chloride; tin(II) chloride dihdyrate; Triisopropyl borate; tin(IV) chloride; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 4: Paal-Knorr pyrrole synthesis / 7: Friedel Crafts acylation;

DOI:10.1016/j.cclet.2011.06.005

upstream raw materials:

2-bromo-4-(pyrrol-1-yl)benzoic acid methyl ester

2-bromo-4-(pyrrol-1-yl)benzyl alcohol

6-(pyrrol-1-yl)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole

benzoyl chloride