2-Fluoro-5-(trifluoromethyl)benzaldehyde → HCID 87426708, compound

HRID 623522Notes

Reaction equation

HRID 623522 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=O.[CH3:14][C:15]([S@@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>ClCCl.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1/[CH:4]=[N:20]/[S@:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19]

Participants

5

Reactant 2

HCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 87426708HCID 87426708, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-fluoro-5-(trifluoromethyl)benzaldehyde (1.00 g, 5.21 mmol), (S)-2-methylpropane-2-sulfinamide (631 mg, 5.21 mmol), and copper sulfate (1.66 g, 10.4 mmol) in dichloromethane is stirred at room temperature for 12 hours. Additional copper sulfate (1.66 g, 10.4 mmol) is added, and the mixture is stirred at room temperature for 5 hours. Then, the mixture is filtered through a pad of Celite, and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (10:1) to give 314 mg (20% yield) of the title compound as colorless oil.

Workup

  1. stirringthe mixture is stirred at room temperature for 5 hours
  2. filtrationThen, the mixture is filtered through a pad of Celite
  3. concentrationthe filtrate is concentrated in vacuo
  4. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (10:1)

Sources & evidence

ORD record
ord-f717d6445384449f94abe3a7e75eb61b
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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