Trifluoroacetic acid → HCID 68293620, compound

HRID 1472780Notes

Reaction equation

HRID 1472780 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[S:13][C:12]([C:14]#[N:15])=[CH:11][C:10]=2[I:16])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[S:13][C:12]([C:14]#[N:15])=[CH:11][C:10]=2[I:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68293607HCID 68293607, compound

Product 1

HCID 68293620HCID 68293620, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round-bottomed flask was charged with 5-((4-chlorophenyl)(hydroxy)methyl)-4-iodothiophene-2-carbonitrile (1.67 g, 4.45 mmol). After degassed, dichloromethane (8 mL), TFA (4 mL) and triethylsilane (1.1 mL, 6.9 mmol) was added sequentially through syringe. The reaction was further stirred at rt until complete, and then concentrated. The residue was purified by flash chromatography (hexane:CH2CL2=2:1). 1.36 g (85%) of product was obtained as a white solid.

Workup

  1. customAfter degassed
  2. concentrationthen concentrated
  3. customThe residue was purified by flash chromatography (hexane:CH2CL2=2:1)

Sources & evidence

ORD record
ord-9f61168d7f6d45738ef8de7d5884c956
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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