Potassium Iodide → HCID 59596828, compound

HRID 1261450Notes

Reaction equation

HRID 1261450 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=1.[C:10]([O:14][C:15](=[O:26])[NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=1)([CH3:13])([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CN(C)C=O>[C:10]([O:14][C:15](=[O:26])[NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=2)[CH:20]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 99743-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 11031911tert-Butyl 3-hydroxyphenethylcarbamate

Product 1

HCID 59596828HCID 59596828, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2.87 g (19.8 mmol) of 1-chloromethyl-3-fluoro-benzene in 5 ml of dry dimethylformamide were added to a suspension of 4.66 g (19.6 mmol) of [2-(3-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester, 4 g of K2CO3 and 0.3 g of potassium iodide in 50 ml of dry dimethylformamide. The reaction was first stirred at room temperature overnight, then was heated up to 50° C. for 6 hours. After evaporation of the solvent, water was added to the residue and the product was extracted with ethyl acetate. 7 g of crude oil were obtained. Purification by flash chromatography using a mixture of ethyl acetate/hexane (1:9→2:8 gradient) gave 5.9 g (86% yield) of the title product as a colourless oil.

Workup

  1. temperaturewas heated up to 50° C. for 6 hours
  2. customAfter evaporation of the solvent, water
  3. additionwas added to the residue
  4. extractionthe product was extracted with ethyl acetate
  5. custom7 g of crude oil were obtained
  6. customPurification by flash chromatography
  7. additiona mixture of ethyl acetate/hexane (1:9→2:8 gradient)

Sources & evidence

ORD record
ord-f1da4ab05fcb498ebd2c5197d70f434e
Source dataset
uspto-grants-2013_06
Patent number
US08470877B2

Reaction notes

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