Iodine → HCID 18451511, compound

HRID 1270714Notes

Reaction equation

HRID 1270714 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].C(=O)(O)[O-].[Na+].[I:15]I>>[F:1][C:2]1[CH:8]=[C:7]([I:15])[CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4]

Participants

4

Reactant 3

HCID 807IodineHCID 516892Sodium BicarbonateHCID 27342052-Chloro-6-fluoroaniline

Product 1

HCID 18451511HCID 18451511, compound

Conditions

Temperature
60 °C

Procedure

2-Fluoro-6-chloroaniline (28.8 g, 0.2 mol) is suspended in a solution of sodium bicarbonate (17.2 g, 0.2 mol in 150 mL water) and warmed to 60° C. Elemental iodine (50.8 g, 0.2 mol) is added portionwise and the resulting mixture stirred at 60° C. for 3 days. After cooling to room temperature, the reaction mixture is partitioned between CH2Cl2 (350 mL) and saturated sodium bisulfite solution (500 mL). The aqueous layer is re-extracted with additional CH2Cl2 (250 mL) and the combined organic layers dried (MgSO4) and concentrated by rotary evaporator. The residual oil is purified by flash chromatography (9:1 hexanes/EtOAc) to give 2-fluoro-4-iodo-6-chloroaniline (m.p. 85–87° C.).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture is partitioned between CH2Cl2 (350 mL) and saturated sodium bisulfite solution (500 mL)
  3. extractionThe aqueous layer is re-extracted with additional CH2Cl2 (250 mL)
  4. dry with materialthe combined organic layers dried (MgSO4)
  5. concentrationconcentrated by rotary evaporator
  6. customThe residual oil is purified by flash chromatography (9:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-dcb9a4d490b14e5983696d3ce374f6a3
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

Loading…