4-(1-trifluoromethyl-1,2-dichloroethylthio)-6-oxatricyclo<3.2.1.1^3,8>nonan-7-one

Base Information

• Chemical Name: 4-(1-trifluoromethyl-1,2-dichloroethylthio)-6-oxatricyclo<3.2.1.1^3,8>nonan-7-one
• CAS No.: 128856-04-2
• Molecular Formula: C₁₁H₁₁Cl₂F₃O₂S
• Molecular Weight: 335.174

Synonyms:4-(1-trifluoromethyl-1,2-dichloroethylthio)-6-oxatricyclo<3.2.1.1^3,8>nonan-7-one

Chemical Property of 4-(1-trifluoromethyl-1,2-dichloroethylthio)-6-oxatricyclo<3.2.1.1^3,8>nonan-7-one

Chemical Property:

Purity/Quality:

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Technology Process of 4-(1-trifluoromethyl-1,2-dichloroethylthio)-6-oxatricyclo<3.2.1.1^3,8>nonan-7-one

There total 2 articles about 4-(1-trifluoromethyl-1,2-dichloroethylthio)-6-oxatricyclo<3.2.1.1^3,8>nonan-7-one 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:

endo-norbornenecarboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) + α-methoxycarbonylhexafluoroisopropylsulfenyl chloride (69162-17-0) + endo-norbornenecarboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) + α-(methoxycarbonyl)tetrafluoroethylsulfenyl chloride (184948-91-2) + 1,1,1-trifluoro-2,3-dichloropropane-2-sulfenyl chloride (106306-29-0) → 4-(α-methoxycarbonylhexafluoroisopropylthio)-6-oxatricyclo<3.2.1.13,8>nonan-7-one (118352-55-9,128946-51-0) + (+/-)-di-tert-butyl 7β-benzyloxycarbonyl-(1α,2β,5β,6α)-tricyclo[4.2.1.02,5]nona-3-ene-3,4-dicarboxylate + 4-(1-trifluoromethyl-1,2-dichloroethylthio)-6-oxatricyclo<3.2.1.13,8>nonan-7-one (128856-04-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N; EDCI; DMAP / CH₂Cl₂ / 12 h / 20 °C

2: RuH₂(CO)(PPh₃) / benzene / 24 h / 80 °C

3: TBHP; t-BuOK / tetrahydrofuran; toluene / 12 h / 20 °C

With tert.-butylhydroperoxide; dmap; potassium tert-butylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; (Ph₃P)Ru(CO)H₂; In tetrahydrofuran; dichloromethane; toluene; benzene; 2: Mitsudo reaction;

DOI:10.1039/b301980b

Reference yield:

endo-norbornenecarboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) + α-methoxycarbonylhexafluoroisopropylsulfenyl chloride (69162-17-0) + endo-norbornenecarboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) + α-(methoxycarbonyl)tetrafluoroethylsulfenyl chloride (184948-91-2) + 1,1,1-trifluoro-2,3-dichloropropane-2-sulfenyl chloride (106306-29-0) → 4-(α-methoxycarbonylhexafluoroisopropylthio)-6-oxatricyclo<3.2.1.13,8>nonan-7-one (118352-55-9,128946-51-0) + (+/-)-di-tert-butyl 7β-benzyloxycarbonyl-(1α,2β,5β,6α)-tricyclo[4.2.1.02,5]nona-3-ene-3,4-dicarboxylate + 4-(1-trifluoromethyl-1,2-dichloroethylthio)-6-oxatricyclo<3.2.1.13,8>nonan-7-one (128856-04-2) + 2,3,3,3-Tetrafluoro-2-((1R,2R,3R,6R,7S)-5-oxo-4-oxa-tricyclo[4.2.1.03,7]non-2-ylsulfanyl)-propionic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 75.8 percent / triethylamine, N-phenylphosphoroamidochloridate / diethyl ether / 0.5 h / Ambient temperature

2: 1.) ZnCl₂ / 1.) ether, 5 min, 2.) ether, 45 min

With N-phenylphosphoroamidochloridate; triethylamine; zinc(II) chloride; In diethyl ether;

DOI:10.1021/jo00234a001

upstream raw materials:

endo-norbornenecarboxylic acid

α-methoxycarbonylhexafluoroisopropylsulfenyl chloride

α-(methoxycarbonyl)tetrafluoroethylsulfenyl chloride

1,1,1-trifluoro-2,3-dichloropropane-2-sulfenyl chloride

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