Potassium Carbonate → 4-[4-Bromo-5-chloro-2-(methyl-o-tolyl-carbamoyl)-phenoxy]-butyric acid tert-butyl ester

HRID 1848612Notizen

Reaktionsgleichung

[Br:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]([OH:19])=[C:6]([CH:18]=1)[C:7]([N:9]([CH3:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:28][CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>CN(C=O)C>[C:34]([O:33][C:31](=[O:32])[CH2:30][CH2:29][CH2:28][O:19][C:5]1[CH:4]=[C:3]([Cl:20])[C:2]([Br:1])=[CH:18][C:6]=1[C:7](=[O:8])[N:9]([CH3:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])([CH3:37])([CH3:36])[CH3:35]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To 5-bromo-4-chloro-2-hydroxy-N-methyl-N-o-tolyl-benzamide (2.6 g, 7.3 mmol) in dry DMF (30 mL), was added K2CO3 (2.0 g, 7.6 mmol), followed by addition of t-butyl 4-bromobutyrate (2.0 g, 8.8 mmol). The mixture was heated at 60° C. for 12 hrs and partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, and dried over MgSO4. After filtration, concentration and purification by silica gel column chromatography eluting with ethyl acetate in hexanes (3/7) gave 4-[4-bromo-5-chloro-2-(methyl-o-tolyl-carbamoyl)-phenoxy]-butyric acid tert-butyl ester (3.0 g). MS: 496.3 (M+H)+; tR=2.81 min (method 1).

Aufarbeitung

custompartitioned between ethyl acetate and water
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over MgSO4
filtrationAfter filtration, concentration and purification by silica gel column chromatography
washeluting with ethyl acetate in hexanes (3/7)

Quellen und Nachweise

ORD-Eintrag: ord-51277fb0521a4b27b384c6e67166fdc1
Quelldatensatz: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08952161B2

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