4-Bromo-2,5-difluoronitrobenzene → HCID 15194586, compound

HRID 1781015Notes

Reaction equation

HRID 1781015 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[F:12].[NH2:13][CH2:14][C:15]([O-:17])=[O:16].[Na+:18]>CN(C=O)C.O>[Na+:18].[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:13][CH2:14][C:15]([O-:17])=[O:16])[CH:7]=1

Participants

5

Reactant 2

HCID 27362864-Bromo-2,5-difluoronitrobenzeneHCID 4684308Sodium Glycinate

Product 1

HCID 15194586HCID 15194586, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 1-bromo-2,5-difluoro-4-nitrobenzene (1.100 g, 4.622 mmol, as prepared above) in DMF (11.0 mL) at 70° C., was added, dropwise, a solution of sodium glycinate (0.451 g, 4.65 mmol, Aldrich, used as received) in water (5.0 mL). The resulting solution was stirred overnight at 70° C. The solution was cooled to room temperature and the bright orange solid was filtered, washed with cold acetone (10 mL) and dried under vacuum to give 0.469 g (35%) of the title compound as a bright orange powder; 1H NMR (DMSO-d6): δ3.458 (d, 2H, J=3.9 Hz), 7.148 (d, 1H, J=6.0 Hz), 7.944 (d, 1H, J=9.3 Hz), 8.740 (s, 1H).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationthe bright orange solid was filtered
  3. washwashed with cold acetone (10 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1bdba27d99f44e589e147105b04a762a
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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