Potassium Iodide → HCID 59596853, compound

HRID 2264649Notes

Reaction equation

HRID 2264649 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:28])[NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH3:27])[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:28])[NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=2)=[C:21]([O:26][CH3:27])[CH:20]=1)([CH3:12])([CH3:13])[CH3:11]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 99743-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 14018350HCID 14018350, compound

Product 1

HCID 59596853HCID 59596853, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

34.6 g (0.23 mol) of 1-chloromethyl-3-fluoro-benzene in 50 ml of dry dimethylformamide were added to a suspension of 55.9 g (0.209 mol) of [2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester, 43 g of K2CO3 and 3.4 g of potassium iodide in 400 ml of dry dimethylformamide. The reaction was stirred at room temperature overnight. Solvent was removed, water was added to the residue and the product was extracted with ethyl acetate. The crude oil obtained was triturated with diethyl ether. The solid was filtered and 58.2 g (74% yield) of the title product were obtained.

Workup

  1. customSolvent was removed
  2. additionwater was added to the residue
  3. extractionthe product was extracted with ethyl acetate
  4. customThe crude oil obtained
  5. customwas triturated with diethyl ether
  6. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-997e90298c6249d090019ed0106d2c15
Source dataset
uspto-grants-2010_12
Patent number
US07855227B2

Reaction notes

Loading…