4-Bromoaniline → HCID 17284186, compound

HRID 593309Notes

Reaction equation

HRID 593309 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1>C1COCC1>[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)=[O:11])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 78074-BromoanilineHCID 27347083,4-Difluorophenyl isocyanate

Product 1

HCID 17284186HCID 17284186, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Difluorophenyl isocyanate (0.74 g, 4.8 mmol) was added to a solution of 4-bromo aniline (0.75 g, 4.36 mmol) in THF (20 mL) and stirred at room temperature for 2 hr. The solvent was removed under reduced pressure and the residue was triturated with chloroform (60 mL) to afford title compound (0.6 g, 42%) as solid. 1H NMR (300 MHz, DMSO-d6): δ 8.9 (s, 1H), 8.87 (s, 1H), 7.64 (m, 1H), 7.47-7.41 (m, 4H), 7.39 (m, 1H), 7.2 (m, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was triturated with chloroform (60 mL)

Sources & evidence

ORD record
ord-8327c9ddcd334fe18bfc7308981b1b55
Source dataset
uspto-grants-2016_01
Patent number
US09242929B2

Reaction notes

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