2,4-Dichlorobenzyl chloride → HCID 71721656, compound

HRID 591475Notes

Reaction equation

HRID 591475 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[S:8][CH2:7]1)[CH3:2].[Cl:17][C:18]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:19]=1[CH2:20]Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:20][C:19]3[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:18]=3[Cl:17])=[CH:14][C:9]=2[S:8][CH2:7]1)[CH3:2]

Participants

6

Reactant 3

HCID 72122,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 59293869HCID 59293869, compound

Product 1

HCID 71721656HCID 71721656, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of ethyl(6-hydroxy-2,3-dihydro-1-benzothiophen-3-yl)acetate (17.2 g) in DMF (300 mL) were added 2,4-dichlorobenzyl chloride (17.0 g) and K2CO3 (15.0 g) and the resulting solution was stirred at 20° C. for 72 h. The mixture was diluted with EtOAc, washed successively with water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc) to give the title compound (19.6 g).

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (PE/EtOAc)

Sources & evidence

ORD record
ord-0494faa88a3240e89e1bd7f9765ba0ed
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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