(4R)-(3,4-Dichlorophenyl)benzenebutanoic acid 1,1-dimethylethyl ester

Base Information

Chemical Name:(4R)-(3,4-Dichlorophenyl)benzenebutanoic acid 1,1-dimethylethyl ester
CAS No.:147189-42-2
Molecular Formula:C₂₀H₂₂Cl₂O₂
Molecular Weight:365.299
Hs Code.:

Synonyms:(4R)-(3,4-Dichlorophenyl)benzenebutanoic acid 1,1-dimethylethyl ester

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Chemical Property of (4R)-(3,4-Dichlorophenyl)benzenebutanoic acid 1,1-dimethylethyl ester

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Technology Process of (4R)-(3,4-Dichlorophenyl)benzenebutanoic acid 1,1-dimethylethyl ester

There total 6 articles about (4R)-(3,4-Dichlorophenyl)benzenebutanoic acid 1,1-dimethylethyl 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: 80.0%

: 20555-91-3
3,4-dichloroiodobenzene

: t-butyl 4-((methylsulfonyl)oxy)-4-phenylbutanoate

: 147189-42-2
(4R)-(3,4-Dichlorophenyl)benzenebutanoic acid 1,1-dimethylethyl ester

Guidance literature:: 3,4-dichloroiodobenzene; With isopropylmagnesium chloride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere; Glovebox;

With zinc(II) iodide; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere; Glovebox;

t-butyl 4-((methylsulfonyl)oxy)-4-phenylbutanoate; With nickel(II) bromide diethylene glycol dimethyl ether; (4R,4'R,5R,5'R)-4,4'-bis(methoxymethyl)-5,5'-diphenyl-4,4',5,5'-tetrahydro-2,2'-bioxazole; lithium iodide; In tetrahydrofuran; dichloromethane; at -40 ℃; for 60h; enantioselective reaction; Inert atmosphere; Glovebox; Sealed tube;
DOI:10.1021/ja408561b

Reference yield:

: 50597-19-8
3-(3,4-dichlorobenzoyl)-propionic acid

: 147189-42-2
(4R)-(3,4-Dichlorophenyl)benzenebutanoic acid 1,1-dimethylethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / H₂SO₄ / various solvent(s) / 18 h

2: BH₃, (S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo<1,2-c><1,3,2>oxazaborole / tetrahydrofuran / 0 °C

3: 97 percent / Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

4: 1) CuCN / 1) Et₂O, a) -20 deg C, 30 min, b) 0 deg C, 30 min, 2) Et₂O, -45 deg C, 16 h

With sulfuric acid; borane; triethylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)88330-7

Reference yield:

: 147189-99-9
4-(3,4-Dichlorophenyl)-4-oxobutanoic acid 1,1-dimethylethyl ester

: 147189-42-2
(4R)-(3,4-Dichlorophenyl)benzenebutanoic acid 1,1-dimethylethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: BH₃, (S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo<1,2-c><1,3,2>oxazaborole / tetrahydrofuran / 0 °C

2: 97 percent / Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

3: 1) CuCN / 1) Et₂O, a) -20 deg C, 30 min, b) 0 deg C, 30 min, 2) Et₂O, -45 deg C, 16 h

With borane; triethylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)88330-7