t-Butyl bromide → Tert-butyl 2-(4-fluoroanilino)-4-nitrobenzoate

HRID 2191624Notes

Reaction equation

CN(C)C(=O)C.[F:7][C:8]1[CH:26]=[CH:25][C:11]([NH:12][C:13]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:34]([CH3:37])([CH3:36])[CH3:35]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C.O>[F:7][C:8]1[CH:26]=[CH:25][C:11]([NH:12][C:13]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:14]=2[C:15]([O:17][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:16])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To N,N-dimethylacetamide 15 mL solution of 2-(4-fluoroanilino)-4-nitrobenzoic acid 1.0 g, were added potassium carbonate 9.9 g, benzyltriethylammonium chloride 0.82 g and 2-bromo-2-methylpropane 21 mL at room temperature, and it was stirred at 55° C. for 4 hours. After the reaction mixture was cooled to room temperature,2-bromo-2-methylpropane 21 mL was added to it, and it was stirred at 55° C. for 12 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with water and 10% citric acid aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=8:1] to give tert-butyl 2-(4-fluoroanilino)-4-nitrobenzoate 1.1 g of red oil.

Workup

additionwas added to it, and it
stirringwas stirred at 55° C. for 12 hours
temperatureAfter the reaction mixture was cooled to room temperature
customThe organic layer was separated
washafter sequential washing with water and 10% citric acid aqueous solution
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-06b2e4c2d8d74843ace974954c3728ae
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08327467B2

Reaction notes

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