Hydrogen Bromide → 1-Bromo-4-fluoro-2-nitrobenzene

HRID 2292268Notes

Reaction equation

HRID 2292268 reaction equation
N([O-])=O.[Na+].[N+:5]([C:8]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:9]=1N)([O-:7])=[O:6].[BrH:16]>O>[N+:5]([C:8]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:9]=1[Br:16])([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 677694-Fluoro-2-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 27733831-Bromo-4-fluoro-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 10 g of sodium nitrite in 30 ml of water were added with stirring at 0° C. to a suspension of 21.6 g of the product of Step B, 69 ml of 48% hydrobromic acid and 138 ml of water and the mixture was stirred at 0° C. for 10 minutes and then added with stirring to a solution of 30 g of cuprous bromide in 105 ml of 48% hydrobromic acid at 60° C. The mixture was stirred at 55°-60° C. for one hour and was poured into ice water. The mixture was extracted with isopropyl ether and the combined organic phases were dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and eluted with methylene chloride. The solution was evaporated to dryness and the residue was dried under reduced pressure to obtain 20.2 g of 2-nitro-4-fluoro-bromobenzene melting at 40°-41° C.

Workup

  1. additionadded
  2. stirringThe mixture was stirred at 55°-60° C. for one hour
  3. extractionThe mixture was extracted with isopropyl ether
  4. customthe combined organic phases were dried
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel
  7. washeluted with methylene chloride
  8. customThe solution was evaporated to dryness
  9. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-592cd301d3744b4ca798ecabc7f89daf
Source dataset
uspto-grants-1989_01
Patent number
US04801717

Reaction notes

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