Acetic Acid → 5-Bromo-1,3-difluoro-2-nitrobenzene

HRID 59931

Reaction equation

HRID 59931 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.[OH2:11].CC(O)=[O:14]>>[Br:1][C:2]1[CH:8]=[C:7]([F:9])[C:5]([N+:6]([O-:14])=[O:11])=[C:4]([F:10])[CH:3]=1

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 962Water3×HCID 6101914-Bromo-2,6-difluoroaniline

Product 1

HCID 213354875-Bromo-1,3-difluoro-2-nitrobenzene

Conditions

Temperature
70 °C

Procedure

A solution of 4-bromo-2,6-difluoroaniline (240 mmol) in AcOH (150 mL) was added dropwise to a suspension of NaBO3.4 H2O (325 mmol) in AcOH (450 mL) at 70° C. during 30 min. Another 2080 mmol of NaBO3.4 H2O were added over 5 h to the mixture. During this period the mixture was stirred at 70° C. The mixture was poured into water and extracted with Et2O. The organic layer was combined with another Et2O solution obtained from another reaction using the same conditions described above. The mixture was concentrated. A precipitate was formed and separated by filtration. The filtrate was concentrated to afford the desired product after flash column chromatography (SiO2, petroleum ether).

Workup

  1. extractionextracted with Et2O
  2. customobtained from another reaction
  3. concentrationThe mixture was concentrated
  4. customA precipitate was formed
  5. customseparated by filtration
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3257fcb39fa44c9aa53c83e4c87efeec
Source dataset
uspto-grants-2016_09
Patent number
US09440929B2

Linked notes

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