(R)-4-(4-chlorophenyl)-4,5-dihydrobenzo[b]oxepin-2(3H)-one

Base Information

• Chemical Name: (R)-4-(4-chlorophenyl)-4,5-dihydrobenzo[b]oxepin-2(3H)-one
• CAS No.: 1446840-67-0
• Molecular Formula: C₁₆H₁₃ClO₂
• Molecular Weight: 272.731
• Mol file: 1446840-67-0.mol

Synonyms:(R)-4-(4-chlorophenyl)-4,5-dihydrobenzo[b]oxepin-2(3H)-one

Chemical Property of (R)-4-(4-chlorophenyl)-4,5-dihydrobenzo[b]oxepin-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-(4-chlorophenyl)-4,5-dihydrobenzo[b]oxepin-2(3H)-one

There total 3 articles about (R)-4-(4-chlorophenyl)-4,5-dihydrobenzo[b]oxepin-2(3H)-one 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: 64.0%

(E)-3-(4-chlorophenyl)acrylaldehyde (41798-44-1,22329-01-7) + 2-((tert-butyldimethylsilyl)oxy)benzyl bromide (105262-86-0) → (R)-4-(4-chlorophenyl)-4,5-dihydrobenzo[b]oxepin-2(3H)-one (1446840-67-0)

Guidance literature:

With 18-crown-6 ether; (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; tetrabutylammonium acetate; cesium fluoride; In tetrahydrofuran; at -18 ℃; for 12h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja405833m

Reference yield:

2-(tert-butyldimethylsilyloxy)toluene (62790-79-8) → (R)-4-(4-chlorophenyl)-4,5-dihydrobenzo[b]oxepin-2(3H)-one (1446840-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 2 h / Inert atmosphere; Reflux

2: tetrabutylammonium acetate; cesium fluoride; 18-crown-6 ether; (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate / tetrahydrofuran / 12 h / -18 °C / Inert atmosphere

With N-Bromosuccinimide; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; tetrabutylammonium acetate; cesium fluoride; In tetrahydrofuran; benzene;

DOI:10.1021/ja405833m

Reference yield:

ortho-cresol (95-48-7,77504-84-8) → (R)-4-(4-chlorophenyl)-4,5-dihydrobenzo[b]oxepin-2(3H)-one (1446840-67-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / Inert atmosphere

2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 2 h / Inert atmosphere; Reflux

3: tetrabutylammonium acetate; cesium fluoride; 18-crown-6 ether; (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate / tetrahydrofuran / 12 h / -18 °C / Inert atmosphere

With 1H-imidazole; N-Bromosuccinimide; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; tetrabutylammonium acetate; cesium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja405833m

upstream raw materials:

(E)-3-(4-chlorophenyl)acrylaldehyde

2-((tert-butyldimethylsilyl)oxy)benzyl bromide

ortho-cresol

2-(tert-butyldimethylsilyloxy)toluene