Dimethylformamide → 4-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)nitrobenzene

HRID 704468

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[CH2:25][C:26]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:27]>O>[Cl:1][C:2]1[C:3]([O:12][CH2:25][C:26]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:27])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-chloro-4-fluoro-5-nitrophenol (100 g), anhydrous potassium carbonate (86.6 g) and dimethylformamide (500 g) was heated at 50° C., and amyl 2-chloroacetate (90.2 g) was dropwise added thereto in 30 minutes, followed by allowing to stand at 60° C. for 4 hours. The reaction mixture was cooled to room temperature, and water (1500 g) was added thereto, followed by extraction with ethyl acetate (1500 g). The organic layer was separated, washed with water and concentrated under reduced pressure. The residue was distilled under reduced pressure to give 4-chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)nitrobenzene (Compound (III)) (129 g) as a pale yellow oil. Yield, 77%. b.p., 160 °-165° C./0.7 mmHg.

Workup

waitto stand at 60° C. for 4 hours
temperatureThe reaction mixture was cooled to room temperature
extractionfollowed by extraction with ethyl acetate (1500 g)
customThe organic layer was separated
washwashed with water
concentrationconcentrated under reduced pressure
distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record: ord-7d833a2fbac6442e9b55822269a7a13a
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04987247

Linked notes

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