(1S,2R,3S,6S,R_S)-2-Chloro-2-fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol

Base Information

• Chemical Name: (1S,2R,3S,6S,R_S)-2-Chloro-2-fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol
• CAS No.: 140148-23-8
• Molecular Formula: C₁₄H₁₈ClFO₂S
• Molecular Weight: 304.813

Synonyms:(1S,2R,3S,6S,R_S)-2-Chloro-2-fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol

Chemical Property of (1S,2R,3S,6S,R_S)-2-Chloro-2-fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol

Chemical Property:

Purity/Quality:

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Technology Process of (1S,2R,3S,6S,R_S)-2-Chloro-2-fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol

There total 3 articles about (1S,2R,3S,6S,R_S)-2-Chloro-2-fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol 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: 26.5%

(2S,3S,RS)-1,1-Dichloro-1-fluoro-3-<(4-methylphenyl)sulfinyl>hept-6-en-2-ol (139965-00-7) → (1S,2R,3S,6S,RS)-2-Chloro-2-fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol (140148-23-8) + (1S,2S,3S,6S,RS)-2-Chloro-2-fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol (139965-02-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 74 ℃; for 5h;

DOI:10.1021/jo00100a057

Reference yield:

(+)-(RS)-5-<(4-Methylphenyl)sulfinyl>pent-1-ene (118558-73-9) → (1S,2R,3S,6S,RS)-2-Chloro-2-fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol (140148-23-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / LDA / tetrahydrofuran / 0.08 h / -65 °C

2: 19 percent / NaBH₄ / methanol; aq. NH₃ / 0.17 h / -20 °C

3: 33.1 percent / tributyltin hydride, AIBN / benzene / 5 h / 74 °C

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; ammonium hydroxide; benzene;

DOI:10.1021/jo00100a057

Reference yield:

(RS)-1,1-Dichloro-1-fluoro-3-<(4-methylphenyl)sulfinyl>hept-6-en-2-one → (1S,2R,3S,6S,RS)-2-Chloro-2-fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol (140148-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 19 percent / NaBH₄ / methanol; aq. NH₃ / 0.17 h / -20 °C

2: 33.1 percent / tributyltin hydride, AIBN / benzene / 5 h / 74 °C

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In methanol; ammonium hydroxide; benzene;

DOI:10.1021/jo00100a057

upstream raw materials:

(2S,3S,R_S)-1,1-Dichloro-1-fluoro-3-<(4-methylphenyl)sulfinyl>hept-6-en-2-ol

(+)-(R_S)-5-<(4-Methylphenyl)sulfinyl>pent-1-ene

Downstream raw materials:

(1R,2S,5S,6R,R_S)-6-fluoro-5-methyl-2-<(4-methylphenyl)sulphinyl>cyclohexan-1-ol

(1R,2R,3S,6S)-2-Fluoro-3-methyl-6-<(4-methylphenyl)thio>cyclohexan-1-ol

(1R,2R,3S,6S)-2-Fluoro-3-methyl-6-<(4-methylphenyl)thio>cyclohexan-1-ol benzoate

(1R,2R,3S,6S,R_S)-2-(Benzyloxy)-1-fluoro-6-methyl-3-<(4-methylphenyl)sulfinyl>cyclohexane

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