Potassium Iodide → HCID 66591078, compound

HRID 1092377Notes

Reaction equation

HRID 1092377 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=1.C(O[C:15](=O)[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)(C)(C)C.C([O-])([O-])=O.[K+].[K+].[I-].[K+].[CH3:37][N:38](C)[CH:39]=[O:40]>>[ClH:1].[F:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][NH:16][CH2:15][C:39]([NH:38][CH3:37])=[O:40])=[CH:20][C:21]=1[O:26][CH3:27]

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228Dimethylformamide2×HCID 99743-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 14018350HCID 14018350, compound

Product 1

HCID 66591078HCID 66591078, compoundYield 74%

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-09843e249c95433cb18b0ad80e42e479
Source dataset
uspto-grants-2012_03
Patent number
US08129427B2

Reaction notes

Loading…