2-Isopropylaniline → 4-Iodo-2-(propan-2-yl)aniline

HRID 986014Notes

Reaction equation

HRID 986014 reaction equation
[I:1]Cl.[CH3:3][CH:4]([C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8])[CH3:5].C([O-])(=O)C.[Na+]>C(O)(=O)C>[I:1][C:11]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([CH:4]([CH3:5])[CH3:3])[CH:12]=1

Participants

5

Reactant 3

HCID 125612-IsopropylanilineHCID 24640Iodine chlorideHCID 517045Sodium Acetate

Product 1

HCID 126679384-Iodo-2-(propan-2-yl)aniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Iodine monochloride (12.9 cm3) was added at room temperature to a stirred solution of 2-[prop-2-yl]-aniline (27.0 g) and sodium acetate (16.4 g) in acetic acid (250 cm3). After 1 hour, volatile material was removed in vacuo and the residue was partitioned between ethyl acetate (200 cm3) and 10% sodium carbonate solution (50 cm3). The dried (MgSO4) organic extract was filtered and evaporated in vacuo to afford an oil which was chromatographed on silica (Merck "MK 60.9385") eluting with hexane. Combination and evaporation of the product containing fractions gave the product as a crude dark unstable oil (38 g) which was not characterised fully but was used directly in Preparation 84.

Workup

  1. customvolatile material was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate (200 cm3) and 10% sodium carbonate solution (50 cm3)
  3. dry with materialThe dried (MgSO4)
  4. extractionorganic extract
  5. filtrationwas filtered
  6. customevaporated in vacuo
  7. customto afford an oil which
  8. customwas chromatographed on silica (Merck "MK 60.9385")
  9. washeluting with hexane
  10. customCombination and evaporation of the product
  11. additioncontaining fractions

Sources & evidence

ORD record
ord-6a071a4aec4d4fd0a48892b03475ad72
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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