5-allyl-2-bromo-3,3-dimethoxy-4-methyl-6-oxo-1,4-cyclohexadienecarbaldehyde

Base Information

Chemical Name:5-allyl-2-bromo-3,3-dimethoxy-4-methyl-6-oxo-1,4-cyclohexadienecarbaldehyde
CAS No.:479633-79-9
Molecular Formula:C₁₃H₁₅BrO₄
Molecular Weight:315.164
Hs Code.:

Synonyms:5-allyl-2-bromo-3,3-dimethoxy-4-methyl-6-oxo-1,4-cyclohexadienecarbaldehyde

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Chemical Property of 5-allyl-2-bromo-3,3-dimethoxy-4-methyl-6-oxo-1,4-cyclohexadienecarbaldehyde

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Technology Process of 5-allyl-2-bromo-3,3-dimethoxy-4-methyl-6-oxo-1,4-cyclohexadienecarbaldehyde

There total 2 articles about 5-allyl-2-bromo-3,3-dimethoxy-4-methyl-6-oxo-1,4-cyclohexadienecarbaldehyde 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: 83.0%

: 67-56-1
methanol

: 479633-78-8
3-allyl-6-bromo-2-hydroxy-4-methylbenzaldehyde

: 479633-79-9
5-allyl-2-bromo-3,3-dimethoxy-4-methyl-6-oxo-1,4-cyclohexadienecarbaldehyde

Guidance literature:: With [bis(acetoxy)iodo]benzene; for 12h;
DOI:10.1039/b205487f

Reference yield:

: 139976-21-9
2-bromo-6-hydroxy-4-methylbenzaldehyde

: 479633-79-9
5-allyl-2-bromo-3,3-dimethoxy-4-methyl-6-oxo-1,4-cyclohexadienecarbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 79 percent / sodium hydride / dimethylformamide / 7 h

2: 66 percent / decahydronaphthalene / 7 h / Heating

3: 83 percent / PhI(OAc)2

With [bis(acetoxy)iodo]benzene; sodium hydride; In N,N-dimethyl-formamide; decalin; 2: Claisen rearrangement;
DOI:10.1021/jo040115b

Reference yield:

: 479633-79-9
5-allyl-2-bromo-3,3-dimethoxy-4-methyl-6-oxo-1,4-cyclohexadienecarbaldehyde

: 479634-13-4
(S)-5-(2-benzyloxyethyl)-4,7-dimethoxy-2,6-dimethylindan-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 26 steps

1.1: 70 percent / zinc; acetic acid / 7 h

2.1: 92 percent / K₂CO₃ / dimethylformamide

3.1: 97 percent / TsOH*H₂O / methanol / Heating

4.1: 95 percent / OsO₄; NaIO₄ / CCl₄; H₂O; 2-methyl-propan-2-ol / 1.5 h

5.1: 95 percent / NaBH₄ / methanol / 1.5 h / 0 °C

6.1: 92 percent / sodium hydride / tetrahydrofuran; various solvent(s) / 0 °C

7.1: 95 percent / Amberlite IR 120 / acetone; H₂O

8.1: 66 percent / Pd(PPh₃)4; CuI / toluene / 40 h / Heating

9.1: Bu₂BOSO₂CF₃; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

9.2: CH₂Cl₂ / 7.5 h

9.3: 87 percent / H₂O₂ / CH₂Cl₂; methanol; H₂O / 1 h / 0 °C / pH 7

10.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h

11.1: 89 percent / n-BuLi / hexane; tetrahydrofuran / 6 h / 0 °C

12.1: 89 percent / iBu₂AlH / CH₂Cl₂ / -78 - 0 °C

13.1: 93 percent / n-Bu₃P / tetrahydrofuran

14.1: 22 mg / H₂O₂ / tetrahydrofuran / 5 h

15.1: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h

16.1: 88 percent / benzylideneruthenium(IV) dichloride based catalyst / CH₂Cl₂ / 20 h / Heating

17.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 20 h

18.1: 85 percent / Bu₃SnH; AIBN / toluene / 1.5 h / 115 °C

19.1: 91 percent / acetic acid / H₂O; tetrahydrofuran / 12 h / 50 °C

20.1: 75 percent / triethylamine; CH₃SO₂Cl / tetrahydrofuran / 3 h

21.1: OsO₄; NaIO₄ / CCl₄; H₂O; 2-methyl-propan-2-ol / 9 h

22.1: NaClO₂*2H₂O; NaH₂PO₄*H₂O; 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol / 3 h

23.1: diethyl ether / 0.17 h / 0 °C

24.1: 31 mg / K₂CO₃ / methanol / 1 h

25.1: 96 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 19 h / Heating

26.1: 73 percent / Bu₃SnH; AIBN / benzene / 1.5 h / Heating

With 2,6-dimethylpyridine; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); tributylphosphine; Amberlite IR 120; benzylideneruthenium(IV) dichloride based catalyst; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene; 8.1: Stille coupling;
DOI:10.1021/jo040115b