4-Bromo-1-fluoro-2-nitrobenzene → HCID 68054129, compound

HRID 406968Notes

Reaction equation

HRID 406968 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:16]=[CH:17][CH:18]=1>CN1CCCC1=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:12][C:13]2[CH:14]=[C:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH:16]=[CH:17][CH:18]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

4

Reactant 2

HCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

Product 1

HCID 68054129HCID 68054129, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-bromo-1-fluoro-2-nitrobenzene (6.0 g, 27 mmol, Aldrich, Cat. No. 539112) and tert-butyl (3-aminophenyl)carbamate (6.7 g, 32 mmol, Aldrich, Cat. No. 53175) in N-methylpyrrolidinone (30 mL) was heated at 150° C. overnight. The solution was cooled to room temperature (r.t.) and quenched with NaHCO3 aqueous solution, then extracted with ethyl acetate twice. The combined organic phases were washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated under reduced pressure to afford the desired compound (10.1 g, 91%). LCMS (M+H)+: m/z=408.0.

Workup

  1. customquenched with NaHCO3 aqueous solution
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f30dd574f47846eaa8a020224085ba67
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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