Nitric Acid → 3,4-Dibromo-2-nitro-(trifluoroacetamido)benzene

HRID 54324Notes

Reaction equation

HRID 54324 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:6][C:7]=1[Br:8].[N+:16]([O-])([OH:18])=[O:17]>OS(O)(=O)=O>[Br:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]([NH:9][C:10](=[O:15])[C:11]([F:12])([F:13])[F:14])[CH:5]=[CH:6][C:7]=1[Br:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 199585863,4-Dibromo-(trifluoroacetamido)benzene

Product 1

HCID 199586043,4-Dibromo-2-nitro-(trifluoroacetamido)benzeneYield 69%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 12.95 g (37.3 mmol) of 3,4-dibromo-(trifluoroacetamido)benzene in 150 mL of conc. H2SO4 cooled at 8° C. was added 7.0 mL of 70% HNO3 (110 mmol) over 30 min. After the addition, the stirring was continued within 10°-12° C. for 1 h and then poured into ice-water (600 mL). The precipitate was collected by vacuum filtration, washed with H2O (6×50 mL), dried at 40° C. under 1 mmHg for 12 h, affording 13.90 g (95%) of the crude product. It was crystallized from hexanes (about 180 mL) to give 10.05 g (69%) of 3,4-dibromo-2-nitro-(trifluoroacetamido)benzene. mp. 107°-9° C. IR (KBr) 3331, 3256, 1745, 1551, 1203, 1141 cm-1. 1H NMR (DMSO-d6) 11.834 (s, 1H), 8.448 (s, 1H), 8.082 (s, 1H).

Workup

  1. additionAfter the addition
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with H2O (6×50 mL)
  4. customdried at 40° C. under 1 mmHg for 12 h
  5. customaffording 13.90 g (95%) of the crude product
  6. customIt was crystallized from hexanes (about 180 mL)

Sources & evidence

ORD record
ord-f96dec499d7443c3aed1908d18df6af4
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Reaction notes

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