3-(4-benzyloxy-2-bromo-5-methoxybenzyl)-2-methyl-4-oxocyclohex-2-enecarboxylic acid methyl ester

Base Information

Chemical Name:3-(4-benzyloxy-2-bromo-5-methoxybenzyl)-2-methyl-4-oxocyclohex-2-enecarboxylic acid methyl ester
CAS No.:891202-07-6
Molecular Formula:C₂₄H₂₅BrO₅
Molecular Weight:473.364
Hs Code.:

Synonyms:3-(4-benzyloxy-2-bromo-5-methoxybenzyl)-2-methyl-4-oxocyclohex-2-enecarboxylic acid methyl ester

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Chemical Property of 3-(4-benzyloxy-2-bromo-5-methoxybenzyl)-2-methyl-4-oxocyclohex-2-enecarboxylic acid methyl ester

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Technology Process of 3-(4-benzyloxy-2-bromo-5-methoxybenzyl)-2-methyl-4-oxocyclohex-2-enecarboxylic acid methyl ester

There total 1 articles about 3-(4-benzyloxy-2-bromo-5-methoxybenzyl)-2-methyl-4-oxocyclohex-2-enecarboxylic acid methyl ester 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: 85.0%

: 35490-07-4,134209-76-0
methyl 2-methyl-4-oxocyclohex-2-enecarboxylate

: 222622-96-0
5-(benzyloxy)-1-bromo-2-(bromomethyl)-4-methoxybenzene

: 891202-07-6
3-(4-benzyloxy-2-bromo-5-methoxybenzyl)-2-methyl-4-oxocyclohex-2-enecarboxylic acid methyl ester

Guidance literature:: methyl 2-methyl-4-oxocyclohex-2-enecarboxylate; With potassium tert-butylate; In tert-butyl alcohol; for 1h;

5-(benzyloxy)-1-bromo-2-(bromomethyl)-4-methoxybenzene; With sodium iodide; In tert-butyl alcohol; for 3h; Heating;
DOI:10.1055/s-2006-926408

Reference yield:

: 891202-07-6
3-(4-benzyloxy-2-bromo-5-methoxybenzyl)-2-methyl-4-oxocyclohex-2-enecarboxylic acid methyl ester

: 3-(4-benzyloxy-2-bromo-5-methoxybenzyl)-2-methyl-4-oxocyclohex-2-enecarboxylic acid

Guidance literature:: With lithium hydroxide; In methanol; at 20 ℃; for 16h;
DOI:10.1055/s-2006-926408

Reference yield:

: 891202-07-6
3-(4-benzyloxy-2-bromo-5-methoxybenzyl)-2-methyl-4-oxocyclohex-2-enecarboxylic acid methyl ester

: cis-6-benzyloxy-7-methoxy-1,1-dimethyl-4a-vinyl-2,3,4,4a,9,9a-hexahydro-1H-fluorene

Guidance literature:: Multi-step reaction with 5 steps

1.1: LiOH*H₂O / aq. methanol / 16 h / 20 °C

2.1: 13.8 g / silica gel / CH₂Cl₂ / 4 h / 90 °C

3.1: CuI / diethyl ether / 0.5 h / -25 °C

3.2: 81 percent / BF₃*Et₂O / diethyl ether / -30 - 0 °C

4.1: t-BuOK / toluene / 2 h / 20 °C

4.2: 94 percent / toluene / 12 h / 20 °C

5.1: 96 percent / PPh₃; K₂CO₃ / Pd(OAc)2 / dimethylformamide / 24 h / 100 °C

With lithium hydroxide; copper(l) iodide; potassium tert-butylate; silica gel; potassium carbonate; triphenylphosphine; palladium diacetate; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 4.2: Wittig olefination / 5.1: Heck cyclization;
DOI:10.1055/s-2006-926408