Sulfuric Acid → 1-Bromo-5-fluoro-2-iodo-3-nitrobenzene

HRID 2379118Notes

Reaction equation

HRID 2379118 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:5](N)=[C:4]([Br:12])[CH:3]=1.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:22].[K+]>O.C(OCC)(=O)C>[I:22][C:5]1[C:4]([Br:12])=[CH:3][C:2]([F:1])=[CH:8][C:7]=1[N+:9]([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 2920042-Bromo-4-fluoro-6-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 194297701-Bromo-5-fluoro-2-iodo-3-nitrobenzeneYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix 4-fluoro-2-bromo-6-nitroaniline (15.5g, 66.0mmol) and 50% sulfuric acid (200mL) and cool to 0°-5° C. Add, by dropwise addition, a solution of sodium nitrite (6.0g, 86.4mmol ) in water (50mL) Stir for 30 minutes and add solid potassium iodide (29g, 173mmol). Take up the product in ethyl acetate (300mL) wash with saturated sodium hydrogen carbonate (2×200mL), saturated sodium metabisulfite (2×200mL) and water (200mL). Dry (MgSO4), evaporate the solvent in vacuo and purify by silica gel chromatography to give 1-iodo-2-nitro-4-fluoro-6-bromobenzene as a yellow crystalline solid (17.81g, 76%); mp 75°-76° C.

Workup

  1. temperaturecool to 0°-5° C
  2. additionAdd, by dropwise addition
  3. washwash with saturated sodium hydrogen carbonate (2×200mL), saturated sodium metabisulfite (2×200mL) and water (200mL)
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-81fff2d4b4604e92bc9e8e853f17c40e
Source dataset
uspto-grants-1994_11
Patent number
US05360814

Reaction notes

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