2,4-Dichlorobenzyl chloride → Methyl(7-chloro-6-((2,4-dichlorobenzyl)oxy)-1-benzofuran-3-yl)acetate

HRID 591466Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[C:13]([Cl:14])[C:8]=2[O:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[Cl:23][C:24]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:25]=1[CH2:26]Cl>CN(C=O)C>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:26][C:25]3[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:24]=3[Cl:23])=[C:13]([Cl:14])[C:8]=2[O:7][CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of methyl(7-chloro-6-hydroxy-1-benzofuran-3-yl)acetate (200 mg) and DMF (dry) (8.0 mL) were added K2CO3 (172 mg) and 2,4-dichlorobenzyl chloride (0.138 mL). The mixture was stirred at 60° C. for 1.5 h. The mixture was quenched with water. The precipitate was collected by filtration and washed with water and hexane to give the title compound (272 mg) as a solid. The solid was crystallized from EtOAc-hexane to give the title compound.

Workup

customThe mixture was quenched with water
filtrationThe precipitate was collected by filtration
washwashed with water and hexane

Sources & evidence

ORD record: ord-af95cb7b3f054b559f1499c9b6b61705
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238639B2

Reaction notes

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