Indole-3-Acetic Acid → [1-(4-Fluorobenzyl)indole-3-yl]acetic acid (4-fluorobenzyl)ester

HRID 1738922Notes

Reaction equation

HRID 1738922 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]([OH:15])=[O:14])=[CH:4]1.[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.O>CS(C)=O>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][O:14][C:13](=[O:15])[CH2:12][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:3]([CH2:21][C:20]3[CH:23]=[CH:24][C:17]([F:16])=[CH:18][CH:19]=3)[CH:4]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 802Indole-3-Acetic AcidHCID 962WaterHCID 96024-Fluorobenzyl chlorideHCID 24758Sodium hydride

Product 1

HCID 21840193[1-(4-Fluorobenzyl)indole-3-yl]acetic acid (4-fluorobenzyl)ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

100 ml dimethylsulfoxide (DMSO) are added to a three-necked flask under an N2 atmosphere, 2.1 g sodium hydride (mineral oil suspension) are added with vigorous stirring and treated dropwise with a solution of 5 g (17.8 mmol) indole-3-acetic acid in 50 ml DMSO. 2.58 g (35.6 mMol) 4-fluorobenzyl chloride are added with further stirring. After 12 hours at 25° C. the reaction mixture is added to 300 ml water and extracted with ether. The organic phase is dried and the solvent is removed under reduced pressure. The residue is purified by column chromatography on silica gel.

Workup

  1. extractionextracted with ether
  2. customThe organic phase is dried
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8369b67bc50d44c3a3c39e6c85691186
Source dataset
uspto-grants-1999_10
Patent number
US05965582

Reaction notes

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