4-Bromo-2-fluoroaniline → HCID 25236836, compound

HRID 2092521Notes

Reaction equation

HRID 2092521 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[N:10]([C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=1)=[C:11]=[O:12]>C(Cl)Cl>[CH2:20]([O:19][C:17](=[O:18])[C:16]1[CH:22]=[CH:23][C:13]([NH:10][C:11]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][C:4]=2[F:9])=[O:12])=[CH:14][CH:15]=1)[CH3:21]

Participants

4

Reactant 2

HCID 1230504-Bromo-2-fluoroanilineHCID 589805Ethyl 4-isocyanatobenzoate

Product 1

HCID 25236836HCID 25236836, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-fluoroaniline (0.5 g, 0.0026 mol) and TEA (0.38 mL, 0.0026 mol) in DCM (15 mL) was added ethyl 4-isocyanatobenzoate (0.503 g, 0.0026 mol). The reaction mixture was stirred at room temperature for 3 h. The white solid was obtained and was filtered and dried to afford the title compound [0.7 g, 70%]; LC-MS (ESI): Calculated mass: 380.0; Observed mass: 381.0 [M+H]+ (RT: 1.78 min).

Workup

  1. customThe white solid was obtained
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-756bff8466e54462a19fcc1ee7b9294d
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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