Bicyclo[2.2.1]heptane-2-carboxylic acid, 5-(benzoyloxy)-3-(chloromethyl)-6-hydroxy-, methyl ester, (2-exo,3-endo,5-exo,6-exo)-

Base Information

• Chemical Name: Bicyclo[2.2.1]heptane-2-carboxylic acid, 5-(benzoyloxy)-3-(chloromethyl)-6-hydroxy-, methyl ester, (2-exo,3-endo,5-exo,6-exo)-
• CAS No.: 77299-94-6
• Molecular Formula: C17H19ClO5
• Molecular Weight: 338.788
• Mol file: 77299-94-6.mol

Synonyms:

Chemical Property of Bicyclo[2.2.1]heptane-2-carboxylic acid, 5-(benzoyloxy)-3-(chloromethyl)-6-hydroxy-, methyl ester, (2-exo,3-endo,5-exo,6-exo)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[2.2.1]heptane-2-carboxylic acid, 5-(benzoyloxy)-3-(chloromethyl)-6-hydroxy-, methyl ester, (2-exo,3-endo,5-exo,6-exo)-

There total 4 articles about Bicyclo[2.2.1]heptane-2-carboxylic acid, 5-(benzoyloxy)-3-(chloromethyl)-6-hydroxy-, methyl ester, (2-exo,3-endo,5-exo,6-exo)- 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: 91.0%

dioxa-3,5 exo phenyl-4 syn carbomethoxy-8 exo chloromethyl-9 endo tricyclo <5.2.1.02,6> decane (68763-57-5,68832-03-1) → carbomethoxy-2 exo chloromethyl-3 endo benzoyloxy-5 exo bromo-6 endo bicyclo<2.2.1>heptane (77299-92-4) + (1S,2R,3R,4R,5R,6S)-6-Benzoyloxy-3-chloromethyl-5-hydroxy-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (77299-93-5) + (1S,2R,3R,4R,5R,6S)-5-Benzoyloxy-3-chloromethyl-6-hydroxy-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (77299-94-6)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; for 23h; Yields of byproduct given; Heating;

DOI:10.1016/0040-4020(80)80151-7

Reference yield:

trityl tetrafluoroborate (341-02-6) + dioxa-3,5 exo phenyl-4 syn carbomethoxy-8 exo chloromethyl-9 endo tricyclo <5.2.1.02,6> decane (68763-57-5,68832-03-1) → triphenylmethyl alcohol (76-84-6) + carbomethoxy-2 exo chloromethyl-3 endo benzoyloxy-5 exo bromo-6 endo bicyclo<2.2.1>heptane (77299-92-4) + (1S,2R,3R,4R,5R,6S)-6-Benzoyloxy-3-chloromethyl-5-hydroxy-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (77299-93-5) + (1S,2R,3R,4R,5R,6S)-5-Benzoyloxy-3-chloromethyl-6-hydroxy-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (77299-94-6)

Guidance literature:

With lithium bromide; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given; 1.) CH₃CN, reflux, 1.33 h, 2.) reflux, 3 h;

DOI:10.1016/0040-4020(80)80151-7

Reference yield:

(+/-)-(1R,2S,3R,4S)-3-hydroxybicyclo[2.2.1]heptan-2-yl benzoate (77085-41-7) + dioxa-3,5 exo phenyl-4 syn carbomethoxy-8 exo chloromethyl-9 endo tricyclo <5.2.1.02,6> decane (68763-57-5,68832-03-1) → bromo-2 exo benzoyloxy-7 syn bicyclo<2.2.1>heptane (77085-38-2,77085-39-3,77085-40-6) + bromo-2 endo benzoyloxy-3 exo bicyclo<2.2.1>heptane (77085-37-1,77341-49-2) + (1S,2R,3R,4R,5R,6S)-6-Benzoyloxy-3-chloromethyl-5-hydroxy-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (77299-93-5) + (1S,2R,3R,4R,5R,6S)-5-Benzoyloxy-3-chloromethyl-6-hydroxy-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (77299-94-6)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; for 25h; Yield given. Further byproducts given. Yields of byproduct given; Heating;

DOI:10.1016/S0040-4020(01)97946-3

upstream raw materials:

N-Bromosuccinimide

trityl tetrafluoroborate

dioxa-3,5 exo phenyl-4 syn carbomethoxy-8 exo chloromethyl-9 endo tricyclo <5.2.1.0^2,6> decane

(+/-)-(1R,2S,3R,4S)-3-hydroxybicyclo[2.2.1]heptan-2-yl benzoate