Nitric Acid → 2-Bromo-1,3-difluoro-4-nitrobenzene

HRID 1731795Notes

Reaction equation

HRID 1731795 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[Br:13]>S(=O)(=O)(O)O>[Br:13][C:7]1[C:6]([F:5])=[C:11]([N+:1]([O-:4])=[O:2])[CH:10]=[CH:9][C:8]=1[F:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1235571-Bromo-2,6-difluorobenzene

Product 1

HCID 137327452-Bromo-1,3-difluoro-4-nitrobenzeneYield 84%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A mixture of 10 ml concentrated HNO3 and 10 ml concentrated H2SO4 was added dropwise with cooling to a stirred solution of 30 g 2,6-difluorobromobenzene in 50 ml of concentrated sulfuric acid. The rate of addition was controlled such that the temperature of the mixture did not rise above 55° C. After the addition was complete the reaction mixture was allowed to stir at room temperature for 2 hours. It was then poured onto ice and the resulting solid was collected by filtration, washed with water and dried, yielding a pale yellow solid, m.p. 50°-51.5° C., 84% yield (31.2 g).

Workup

  1. additionwas added dropwise
  2. additionThe rate of addition
  3. customdid not rise above 55° C
  4. additionAfter the addition
  5. additionIt was then poured onto ice
  6. filtrationthe resulting solid was collected by filtration
  7. washwashed with water
  8. customdried
  9. customyielding a pale yellow solid, m.p. 50°-51.5° C., 84% yield (31.2 g)

Sources & evidence

ORD record
ord-4b38ccdb7ad84368b9e2cc1240d551be
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

Loading…