Trifluoroacetic acid → HCID 67071307, compound

HRID 2263978Notes

Reaction equation

HRID 2263978 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([O:13][CH3:14])([CH3:12])[CH3:11])[CH:5]=1)[CH3:2].[I:15]N1C(=O)CCC1=O.FC(F)(F)C(O)=O>C(#N)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]([O:13][CH3:14])([CH3:11])[CH3:12])[CH:7]=[CH:8][C:9]=1[I:15])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 670715551-Ethoxy-3-(1-methoxy-1-methylethyl)benzene

Product 1

HCID 67071307HCID 67071307, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-ethoxy-3-(1-methoxy-1-methyl-ethyl)-benzene (5.15 g, 26.51 mmol) in acetonitrile (60 mL) were added N-iodosuccinimide (8.349 g, 37.11 mmol) and trifluoroacetic acid (1.02 mL, 13.26 mmol). The mixture was stirred at room temperature overnight. It was then concentrated in vacuo and the residue was taken in ethyl acetate. After washing with saturated solution of sodium bicarbonate, water and brine, the organic layer was dried over anhydrous sodium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo to give 9.39 g of 2-ethoxy-1-iodo-4-(1-methoxy-1-methyl-ethyl)-benzene as light brown oil.

Workup

  1. concentrationIt was then concentrated in vacuo
  2. washAfter washing with saturated solution of sodium bicarbonate, water and brine
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. filtrationThe solids were filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-aea191065e9f4f6995b8a32dd4c7f631
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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