Water → Ethyl 2-amino-4-bromo-6-(trifluoromethyl)phenyl(2,4-dimethoxybenzyl)carbamate

HRID 495660

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([N:12]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=2[O:27][CH3:28])[C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:4]([N+:29]([O-])=O)[CH:3]=1.C(=O)(O)[O-].[Na+].O>CO.[Cl-].[Ti+3].[Cl-].[Cl-]>[NH2:29][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]=1[N:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[O:27][CH3:28])[C:13](=[O:17])[O:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl(2,4-dimethoxybenzyl)carbamate (1.204 g) in methanol (90 ml) was added titanium(III) chloride solution (20% wt) (31.5595 g) in an ice bath. The reaction mixture was stirred for 20 minutes at 0° C. To the reaction mixture were added saturated aqueous sodium bicarbonate solution and water, and the mixture was extracted 5 times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (1.1345 g, quantitative yield).

Workup

extractionthe mixture was extracted 5 times with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f200675a2266465fa60dab2413d8f347
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939887B2

Linked notes

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