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

HRID 1600723Notes

Reaction equation

HRID 1600723 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): δ 3.458 (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-a1f9b20819ed4b14bd5d8d466221cc7b
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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