Iodoethane → HCID 14692897, compound

HRID 2248447Notes

Reaction equation

HRID 2248447 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([Cl:18])[C:16]=1[F:17])[C:11]([OH:13])=[O:12].[CH2:19](I)[CH3:20]>CN(C)C=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([Cl:18])[C:16]=1[F:17])[C:11]([O:13][CH2:19][CH3:20])=[O:12]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 199713033,5-Dichloro-4-fluorobenzoic acid

Product 1

HCID 14692897HCID 14692897, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (36 g, 0.26 moles) was added to a stirred mixture of 3,5-dichloro-4-fluorobenzoic acid (27.6 g, 0.13 moles), ethyl iodide (41.2 g-0.26 moles) and dry dimethylformamide (300 ml) under nitrogen. The reaction was heated to 80° C. for 6 hours. The dimethylformamide was removed in vacuo and the residue treated with water (200 ml) acidified with dilute hydrochloric acid and extracted with ethylacetate (2×250 ml). The organic layer was washed with water, dried over magnesium sulphate and evaporated in vacuo, to give an orange oil which was purified by chromatography on silica, using a 4:1 mixture of petrol and diethylether as eluent. The pink oil obtained crystallised on standing, and washing with ice-cold 40-60 petrol gave white crystals of ethyl 3,5-dichloro-4-fluorobenzoate (29 g).

Workup

  1. customThe dimethylformamide was removed in vacuo
  2. additionthe residue treated with water (200 ml)
  3. extractionextracted with ethylacetate (2×250 ml)
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in vacuo
  7. customto give an orange oil which
  8. customwas purified by chromatography on silica
  9. additiona 4:1 mixture of petrol and diethylether as eluent
  10. customThe pink oil obtained
  11. customcrystallised
  12. washwashing with ice-cold 40-60 petrol

Sources & evidence

ORD record
ord-51c9ad5f91054bee866302c136578331
Source dataset
uspto-grants-1991_08
Patent number
US05039807

Reaction notes

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