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Hydrochloric Acid → 1,1'-Thiodi-[5-(2,6-dichloro-4-trifluoromethylphenyl)-2-methylbenzene]

HRID 498964
Notes
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Reaction equation

HRID 498964 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([Cl:18])[C:9]=1[C:19]1[CH:20]=[CH:21][C:22]([CH3:29])=[C:23]([S:25](Cl)(=O)=O)[CH:24]=1.[ClH:30]>C(OCC)C>[S:25]([C:23]1[CH:24]=[C:19]([C:9]2[C:10]([Cl:30])=[CH:11][C:12]([C:14]([F:16])([F:17])[F:15])=[CH:13][C:8]=2[Cl:7])[CH:20]=[CH:21][C:22]=1[CH3:29])[C:23]1[CH:24]=[C:19]([C:9]2[C:8]([Cl:7])=[CH:13][C:12]([C:14]([F:17])([F:16])[F:15])=[CH:11][C:10]=2[Cl:18])[CH:20]=[CH:21][C:22]=1[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 221709435-(2,6-Dichloro-4-trifluoromethylphenyl)-2-methylbenzenesulfonyl chloride

Product 1

HCID 221709441,1'-Thiodi-[5-(2,6-dichloro-4-trifluoromethylphenyl)-2-methylbenzene]Yield 75%

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent
2×

Procedure

To 0.7 g (18.4 mmol) of lithium aluminum hydride in 30 ml of diethyl ether, 7.2 g (17.8 mmol) of 5-(2,6-dichloro-4-trifluoromethylphenyl)-2-methylbenzenesulfonyl chloride in 30 ml of diethyl ether was added dropwise at −10° C. After 12 hours of stirring at room temperature, the reaction mixture was poured into 1N aqueous hydrochloric acid for separation. The organic layer was washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography affored 4.3 g of 1,1′-thiodi-[5-(2,6-dichloro-4-trifluoromethylphenyl)-2-methylbenzene] (yield 75.0%) as a pale yellow dough (nD20 1.6066), which was used in Example 2 (1) as the starting material.

Workup

  1. washThe organic layer was washed with 50 ml of water twice
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2239655c1eed4c999c47691f86d14d42
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07767626B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes