1-{5-[4-(benzyloxy)phenyl]pent-4-ynyloxy}-2-bromo-4-chloro-5-methoxybenzene

Base Information

• Chemical Name: 1-{5-[4-(benzyloxy)phenyl]pent-4-ynyloxy}-2-bromo-4-chloro-5-methoxybenzene
• CAS No.: 1352658-14-0
• Molecular Formula: C₂₅H₂₂BrClO₃
• Molecular Weight: 485.805

Synonyms:1-{5-[4-(benzyloxy)phenyl]pent-4-ynyloxy}-2-bromo-4-chloro-5-methoxybenzene

Chemical Property of 1-{5-[4-(benzyloxy)phenyl]pent-4-ynyloxy}-2-bromo-4-chloro-5-methoxybenzene

Chemical Property:

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Technology Process of 1-{5-[4-(benzyloxy)phenyl]pent-4-ynyloxy}-2-bromo-4-chloro-5-methoxybenzene

There total 1 articles about 1-{5-[4-(benzyloxy)phenyl]pent-4-ynyloxy}-2-bromo-4-chloro-5-methoxybenzene 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: 50.0%

trimethylene oxide (503-30-0) + 1-(benzyloxy)-4-(bromoethynyl)benzene (1352658-13-9) + 5-chloro-4-methoxy-2-(trimethylsilyl)phenyl triflate (1352658-12-8) → 1-{5-[4-(benzyloxy)phenyl]pent-4-ynyloxy}-2-bromo-4-chloro-5-methoxybenzene (1352658-14-0)

Guidance literature:

With potassium fluoride; 18-crown-6 ether; In 1,2-dimethoxyethane; at -15 ℃; for 27h; regioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201104858

Reference yield: 99.0%

1-{5-[4-(benzyloxy)phenyl]pent-4-ynyloxy}-2-bromo-4-chloro-5-methoxybenzene (1352658-14-0) + bis(pinacol)diborane (73183-34-3) → (Z)-2,2'-{1-[4-(benzyloxy)phenyl]-5-(2-bromo-4-chloro-5-methoxyphenoxy)pent-1-ene-1,2-diyl}bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (1352658-15-1)

Guidance literature:

With tetrakis(triphenylphosphine)platinum⁽⁰⁾; In N,N-dimethyl-formamide; at 80 ℃; for 22h;

DOI:10.1002/anie.201104858

Reference yield: 99.0%

1-{5-[4-(benzyloxy)phenyl]pent-4-ynyloxy}-2-bromo-4-chloro-5-methoxybenzene (1352658-14-0) + bis(pinacol)diborane (73183-34-3) → (CH3O)(Cl)(Br)C6H2O(CH2)3C(BO2C2(CH3)4)C(BO2C2(CH3)4)C6H4OCH2C6H5

Guidance literature:

tetrakis(triphenylphosphine)platinum; In N,N-dimethyl-formamide; 80°C, 22 h;

DOI:10.1002/anie.201104858

upstream raw materials:

trimethylene oxide

1-(benzyloxy)-4-(bromoethynyl)benzene

5-chloro-4-methoxy-2-(trimethylsilyl)phenyl triflate

Downstream raw materials:

(E)-5-[4-(benzyloxy)benzylidene]-7-chloro-8-methoxy-2,3,4,5-tetrahydrobenzo[b]oxepine

4-[(7-chloro-8-methoxy-2,3,4,5-tetrahydrobenzo[b]oxepin-5-yl)methyl]phenol

4-[(8-methoxy-2,3,4,5-tetrahydrobenzo[b]oxepin-5-yl)methyl]phenol

(Z)-2,2'-{1-[4-(benzyloxy)phenyl]-5-(2-bromo-4-chloro-5-methoxyphenoxy)pent-1-ene-1,2-diyl}bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

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