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

HRID 1857396Notes

Reaction equation

HRID 1857396 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-1ef74d9dd23b4e069ef35bdba3283e88
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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