(1S,2S)-trans-1-benzoyloxy-2-bromocyclohexane

Base Information

• Chemical Name: (1S,2S)-trans-1-benzoyloxy-2-bromocyclohexane
• CAS No.: 222851-77-6
• Molecular Formula: C₁₃H₁₅BrO₂
• Molecular Weight: 283.165
• Mol file: 222851-77-6.mol

Synonyms:(1S,2S)-trans-1-benzoyloxy-2-bromocyclohexane

Chemical Property of (1S,2S)-trans-1-benzoyloxy-2-bromocyclohexane

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of (1S,2S)-trans-1-benzoyloxy-2-bromocyclohexane

There total 4 articles about (1S,2S)-trans-1-benzoyloxy-2-bromocyclohexane 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: 50.0%

2-bromocyclocyclohexanol (2425-33-4,16536-57-5,24796-87-0,53023-24-8,53023-25-9,60933-67-7,5537-67-7) + benzoyl chloride (98-88-4) → trans-2-bromocyclohexan-1-ol (53023-25-9,5537-67-7) + (1S,2S)-trans-1-benzoyloxy-2-bromocyclohexane (222851-77-6)

Guidance literature:

With triethylamine; (S)-1-methyl-2-[(dihydroisoindol-2-yl)methyl]pyrrolidine; In dichloromethane; at -78 ℃; enantioselective reaction; Molecular sieve; Resolution of racemate;

DOI:10.15227/orgsyn.083.0070

Reference yield:

benzoic acid (65-85-0,8013-63-6) + cyclohexene (110-83-8) → (1S,2S)-trans-1-benzoyloxy-2-bromocyclohexane (222851-77-6) + (1R,2R)-trans-1-benzoyloxy-2-bromocyclohexane (61198-62-7,86236-87-5,122897-84-1)

Guidance literature:

With N-Bromosuccinimide; (R)‐3,3′‐bis(9‐phenanthryl)‐1,1′‐binaphthalene‐2,2′‐diyl hydrogen phosphate; In dichloromethane; cyclohexane; at -40 ℃; for 48.5h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.02.016

Reference yield:

2-bromocyclohexanone (1056477-06-5,822-85-5) + benzoyl chloride (98-88-4) → (1S,2R)-2-bromocyclohexyl benzoate + (1R,2S)-2-bromocyclohexyl benzoate + (1S,2S)-trans-1-benzoyloxy-2-bromocyclohexane (222851-77-6) + (1R,2R)-trans-1-benzoyloxy-2-bromocyclohexane (61198-62-7,86236-87-5,122897-84-1)

Guidance literature:

2-bromocyclohexanone; With chloro {[(1S,2S)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido}(mesitylene)ruthenium(II); tetrabutylammomium bromide; sodium formate; In dichloromethane; water; at 20 ℃; for 24h;

benzoyl chloride; With pyridine; In dichloromethane; at 20 ℃; for 2h; Title compound not separated from byproducts;

DOI:10.1021/ol052821k

upstream raw materials:

2-bromocyclohexanone

benzoyl chloride

benzoic acid

cyclohexene

Downstream raw materials:

(S)-2-cyclohexenyl benzoate