Hydrochloric Acid → 2-Bromo-1-fluoro-4-iodobenzene

HRID 606821Notes

Reaction equation

HRID 606821 reaction equation
N([O-])=O.[Na+].[Br:5][C:6]1[CH:7]=[C:8](N)[CH:9]=[CH:10][C:11]=1[F:12].Cl.[I-:15].[K+]>O>[Br:5][C:6]1[CH:7]=[C:8]([I:15])[CH:9]=[CH:10][C:11]=1[F:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 27792863-Bromo-4-fluoroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 27569802-Bromo-1-fluoro-4-iodobenzeneYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Add at 0° C. a solution of sodium nitrite (2.0 g, 28.9 mmol) in water (15 mL) to a suspension of 3-bromo-4-fluorophenylamine (5.0 g, 26.3 mmol) in a 6 N aqueous solution of hydrochloric acid (25 mL) at 0° C. slowly over 10 min. Stir the mixture at 0° C. for 5 min. Add this solution to a solution of potassium iodide (4.37 g, 26.3 mmol) in water (125 mL) via syringe at 0° C. under nitrogen over 15 min. Stir at 0° C. for 30 min. Warm to room temperature. Extract with four times with dichloromethane (100 mL), dry (sodium sulfate), filter, and concentrate. Purify by silica gel chromatography, eluting with 100:0 to 95:5 hexanes:ethyl acetate to give the title compound as a colorless oil (5.83 g, 74%).

Workup

  1. stirringStir at 0° C. for 30 min
  2. temperatureWarm to room temperature
  3. extractionExtract with four times with dichloromethane (100 mL)
  4. dry with materialdry (sodium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by silica gel chromatography
  8. washeluting with 100:0 to 95:5 hexanes

Sources & evidence

ORD record
ord-6ea14e988f6d47f0b9398cc9885199fc
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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