4-Bromo-3-(trifluoromethyl)aniline → 1-(3-Fluoro-5-trifluoromethyl-phenyl)-3-(4-bromo-3-trifluoromethyl-phenyl)-urea

HRID 642798

Reaction equation

HRID 642798 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[F:13][C:14]1[CH:15]=[C:16]([N:24]=[C:25]=[O:26])[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1>C1COCC1>[F:13][C:14]1[CH:15]=[C:16]([NH:24][C:25]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([Br:1])=[C:3]([C:9]([F:10])([F:11])[F:12])[CH:4]=2)=[O:26])[CH:17]=[C:18]([C:20]([F:22])([F:23])[F:21])[CH:19]=1

Participants

4

Reactant 2

HCID 678524-Bromo-3-(trifluoromethyl)anilineHCID 34456721-Fluoro-3-isocyanato-5-(trifluoromethyl)benzene

Product 1

HCID 167552221-(3-Fluoro-5-trifluoromethyl-phenyl)-3-(4-bromo-3-trifluoromethyl-phenyl)-ureaYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-Bromo-3-(trifluoromethyl)-aniline (132 mg, 0.55 mmol, 1.1 eq.) in dry THF (5 ml) was added 3-Fluoro-5-(trifluoromethyl)-phenylisocyanate (72 μl, 0.5 mmol). After stirring overnight at rt the mixture was diluted with cHexane (20 ml), washed twice with 2 N HCl, once with sat. NaHCO3 and brine (20 ml each) and adsorbed on Celite in vacuo. Flash chromatography on silica with cHexane/TBME (4:1 to 2:1) yielded 111 mg product (50%) as a white powder.

Workup

  1. additionwas diluted with cHexane (20 ml)
  2. washwashed twice with 2 N HCl, once with sat. NaHCO3 and brine (20 ml each)

Sources & evidence

ORD record
ord-29feb1b45952493eafc4fc230a645307
Source dataset
uspto-grants-2010_04
Patent number
US07696249B2

Linked notes

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