(2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid

Base Information

Chemical Name:(2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid
CAS No.:566202-75-3
Molecular Formula:C₂₂H₁₇BrO₄
Molecular Weight:425.279
Hs Code.:

Synonyms:(2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid

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Chemical Property of (2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid

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Technology Process of (2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid

There total 9 articles about (2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid 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: 90.0%

: 2-(4-Benzyloxy-phenyl)-5-bromo-2,3-dihydro-benzofuran-3-carboxylic acid (R)-1-methyl-2-oxo-2-pyrrolidin-1-yl-ethyl ester

: 566202-75-3
(2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid

Guidance literature:: With barium dihydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 3h;
DOI:10.1021/ja036011k

Reference yield: 90.0%

: 566202-74-2
(1'R,2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid 1'-methyl-2'-oxo-2'-pyrrolidin-1'-ylethyl ester

: 566202-75-3
(2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid

Guidance literature:: With barium dihydroxide; In tetrahydrofuran; methanol; at 0 - 20 ℃;
DOI:10.1016/j.tet.2004.06.144

Reference yield:

: 4397-53-9
p-benzyloxybenzaldehyde

: 566202-75-3
(2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / NaBH₄ / tetrahydrofuran; H₂O

2.1: 98 percent / SOCl₂

3.1: 95 percent / K₂CO₃ / dimethylformamide / 4 h / 60 °C

4.1: O₃ / CH₂Cl₂; methanol / 7.5 h / -78 °C

4.2: Me₂S / CH₂Cl₂; methanol / -78 - 20 °C

5.1: 137 g / 2-methyl-2-butene; NaH₂PO₄*2H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 84 h / 20 °C

6.1: 80 percent / diethyl azodicarboxylate; PPh₃ / toluene / 0 - 20 °C

7.1: p-acetamidobenzenesulfonyl azide; DBU / acetonitrile / 0 - 20 °C

8.1: 5.10 g / Rh₂(S-DOSP)4 / CH₂Cl₂ / 0.5 h / 0 °C

9.1: 90 percent / Ba(OH)2*8H₂O / tetrahydrofuran; methanol / 0 - 20 °C

With barium dihydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; 4-acetamidobenzenesulfonyl azide; potassium carbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 6.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2004.06.144