Water → Methyl 2-(3-chloro-4-(6-nitro-1,3-dioxoisoindolin-5-yloxy)phenyl)acetate

HRID 2423322Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[NH:8][C:6](=[O:7])[C:5]2=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14].[Cl:16][C:17]1[CH:18]=[C:19]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:20]=[CH:21][C:22]=1[OH:23].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:16][C:17]1[CH:18]=[C:19]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:20]=[CH:21][C:22]=1[O:23][C:2]1[CH:3]=[C:4]2[C:5](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6](=[O:7])[NH:8][C:9]2=[O:10]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 4-chloro-5-nitrophthalimide (1.05 g, 4.4 mmol), methyl 2-(3-chloro-4-hydroxyphenyl)acetate (821 mg, 4.4 mmol) and potassium carbonate (1.34 g, 9.7 mmol) in 10 mL of DMSO was allowed to stir at 25° C. for 22 h. Upon completion, the mixture was added to 50 mL of water. The resulting mixture was extracted with ethyl acetate (2×30 ml,). The combined extracts were washed with water (2×30 mL) and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was purified by chromatography on a silica gel column using 20% EtOAc/hexane as the eluent to give methyl 2-(3-chloro-4-(6-nitro-1,3-dioxoisoindolin-5-yloxy)phenyl)acetate (30.1). MS ESI (pos.) m/e calcd for (M+H)+ 391.0. found 391.0.

Workup

extractionThe resulting mixture was extracted with ethyl acetate (2×30 ml,)
washThe combined extracts were washed with water (2×30 mL) and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record: ord-7318ff774c8d46e58ebc44c8609ce243
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960567B2

Reaction notes

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