2-chloro-3-[N-methyl-(2-trimethylsilyl-ethyl)-carbamato]-5-(5-bromo-2-methyl-(E,E)-2,4-pentadienyl)-anisole

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Chemical Name:2-chloro-3-[N-methyl-(2-trimethylsilyl-ethyl)-carbamato]-5-(5-bromo-2-methyl-(E,E)-2,4-pentadienyl)-anisole
CAS No.:71653-15-1
Molecular Formula:C₂₀H₂₉BrClNO₃Si
Molecular Weight:474.898
Hs Code.:

Synonyms:2-chloro-3-[N-methyl-(2-trimethylsilyl-ethyl)-carbamato]-5-(5-bromo-2-methyl-(E,E)-2,4-pentadienyl)-anisole

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Chemical Property of 2-chloro-3-[N-methyl-(2-trimethylsilyl-ethyl)-carbamato]-5-(5-bromo-2-methyl-(E,E)-2,4-pentadienyl)-anisole

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Technology Process of 2-chloro-3-[N-methyl-(2-trimethylsilyl-ethyl)-carbamato]-5-(5-bromo-2-methyl-(E,E)-2,4-pentadienyl)-anisole

There total 12 articles about 2-chloro-3-[N-methyl-(2-trimethylsilyl-ethyl)-carbamato]-5-(5-bromo-2-methyl-(E,E)-2,4-pentadienyl)-anisole 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:

: 71653-12-8
(2E,4E)-5-bromo-2-methyl-penta-2,4-dienoic acid ethyl ester

: 71653-15-1
2-chloro-3-[N-methyl-(2-trimethylsilyl-ethyl)-carbamato]-5-(5-bromo-2-methyl-(E,E)-2,4-pentadienyl)-anisole

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) diisobutylaluminum hydride; 2.) water; 3.) sodium sulfite / 1.) hexane, 0 deg C, 1.5 h; 2.) 0 deg C, 30 min; 3.) 0 deg C, 1.75 h

2: 81 percent / N-bromosuccinimide, dimethyl sulfide / CH₂Cl₂ / 3 h / 0 °C

3: 1.) n-BuLi, 2.) pentynylcopper, hexamethylphoshpotriamide / 1.) THF, hexane, -110 deg C -> -78 deg C; -78 deg C, 1.5 h, 2.) -78 deg C, 2.5 h, 3.) -78 deg C, 4.5 h

With 1-pentynyl copper; N,N,N,N,N,N-hexamethylphosphoric triamide; N-Bromosuccinimide; n-butyllithium; dimethylsulfide; water; diisobutylaluminium hydride; sodium sulfite; In dichloromethane;
DOI:10.1021/ja00353a027

Reference yield:

: 3943-74-6
4-hydroxy-3-methoxybenzoic acid methyl ester

: 71653-15-1
2-chloro-3-[N-methyl-(2-trimethylsilyl-ethyl)-carbamato]-5-(5-bromo-2-methyl-(E,E)-2,4-pentadienyl)-anisole

Guidance literature:: Multi-step reaction with 9 steps

1: 74 percent / HNO₃, glacial acetic acid / acetic acid / 2 h / Ambient temperature

2: 88 percent / oxalyl chloride / dimethylformamide / -20 deg C; 80 deg C, 3 h

3: 30 g / KOH / ethanol; H₂O / 2 h / 80 °C

4: 60 percent / mercuric oxide, bromine / CCl₄ / 5 h / Irradiation

5: 1.) iron, 2.) HCl / 1.) ethanol, water, 2.) reflux, 12 h

6: 67 percent / aniline, pyridine / CH₂Cl₂ / 1.) 0 deg C, 10 min; 2.) room temperature, 1 h

7: t-BuOK / tetrahydrofuran / Ambient temperature

8: 1.) t-BuOK / 1.) THF, 0 deg C, 30 min, 2.) room temperature

9: 1.) n-BuLi, 2.) pentynylcopper, hexamethylphoshpotriamide / 1.) THF, hexane, -110 deg C -> -78 deg C; -78 deg C, 1.5 h, 2.) -78 deg C, 2.5 h, 3.) -78 deg C, 4.5 h

With pyridine; 1-pentynyl copper; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; n-butyllithium; oxalyl dichloride; potassium tert-butylate; bromine; nitric acid; iron; acetic acid; aniline; mercury(II) oxide; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/ja00353a027

Reference yield:

: 63603-16-7
2-chloro-3-nitro-5-bromoanisole

: 71653-15-1
2-chloro-3-[N-methyl-(2-trimethylsilyl-ethyl)-carbamato]-5-(5-bromo-2-methyl-(E,E)-2,4-pentadienyl)-anisole

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) iron, 2.) HCl / 1.) ethanol, water, 2.) reflux, 12 h

2: 67 percent / aniline, pyridine / CH₂Cl₂ / 1.) 0 deg C, 10 min; 2.) room temperature, 1 h

3: t-BuOK / tetrahydrofuran / Ambient temperature

4: 1.) t-BuOK / 1.) THF, 0 deg C, 30 min, 2.) room temperature

5: 1.) n-BuLi, 2.) pentynylcopper, hexamethylphoshpotriamide / 1.) THF, hexane, -110 deg C -> -78 deg C; -78 deg C, 1.5 h, 2.) -78 deg C, 2.5 h, 3.) -78 deg C, 4.5 h

With pyridine; 1-pentynyl copper; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; potassium tert-butylate; iron; aniline; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00353a027