Citric Acid → 2-(3-Fluoro-4-nitro-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 1678652Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10](=[O:15])[C:11](Br)([CH3:13])[CH3:12])[CH3:8].[F:16][C:17]1[CH:18]=[C:19]([OH:26])[CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O.CCOC(C)=O>[CH2:7]([O:9][C:10](=[O:15])[C:11]([O:26][C:19]1[CH:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:17]([F:16])[CH:18]=1)([CH3:13])[CH3:12])[CH3:8]

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium carbonate (3.96 g, 29 mmol) and 2-bromo-2-methylpropanoic acid ethyl ester (4.47 g, 23 mmol; CAS Reg. No. 600-00-0) were added to a solution of 3-fluoro-4-nitrophenol (3 g, 19 mmol; CAS Reg. No. 394-41-2) in DMSO (50 ml). The mixture was stirred for 18 h at 100° C. 10% aqueous citric acid and EtOAc were added and the layers were separated. The organic layer was washed with brine and dried over MgSO4. The solid was filtered off and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, EtOAc/heptane) to obtain the title compound (1.19 g, 4.4 mmol; 23%) as yellow oil.

Workup

customthe layers were separated
washThe organic layer was washed with brine
dry with materialdried over MgSO4
filtrationThe solid was filtered off
concentrationthe filtrate concentrated under reduced pressure
customThe residue was purified by column chromatography (silica gel, EtOAc/heptane)

Sources & evidence

ORD record: ord-787e443081614e2d958020cbbc7c29b3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008505B2

Reaction notes

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