Iodoethane → HCID 45094817, compound

HRID 854349Notes

Reaction equation

HRID 854349 reaction equation
[CH2:1]([Li])[CH2:2]CC.[C:6]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1Br)([CH3:9])([CH3:8])[CH3:7].C(I)C>C1COCC1>[C:6]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[CH2:1][CH3:2])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 2829923-bromo-4-tert-butylbenzoic acidHCID 178418339Butyllithium

Product 1

HCID 45094817HCID 45094817, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyl lithium (1.6M in hexane, 2.67 mL, 4.27 mmol) was added dropwise to a solution of 4-tert-butyl-3-bromobenzoic acid (500 mg, 1.94 mmol) in THF at −78° C. whilst maintaining the temperature below −70° C. After 40 minutes, ethyl iodide (1.55 mL, 19.4 mmol) was added dropwise whilst maintaining the temperature below −65° C. After one hour at −70° C., the mixture was allowed to attain room temperature and stirred overnight The mixture was quenched by the addition of saturated ammonium chloride solution (30 mL) and extracted with ether (30 mL). The organic fraction was dried over magnesium sulphate and evaporated. Purification was achieved by reverse phase HPLC on a C18 column using a two-solvent gradient elution with (A) water containing formic acid (0.1%) and (B) acetonitrile-water (95:5 v/v) containing formic acid (0.05%) as the eluents, and analysis of the fractions by electrospray mass spectroscopy. This afforded the title compound as a solid.

Workup

  1. temperaturewhilst maintaining the temperature below −70° C
  2. temperaturewhilst maintaining the temperature below −65° C
  3. waitAfter one hour at −70° C.
  4. customto attain room temperature
  5. customwas quenched by the addition of saturated ammonium chloride solution (30 mL)
  6. extractionextracted with ether (30 mL)
  7. dry with materialThe organic fraction was dried over magnesium sulphate
  8. customevaporated
  9. customPurification
  10. washa two-solvent gradient elution with (A) water
  11. additioncontaining formic acid (0.1%) and (B) acetonitrile-water (95:5 v/v)
  12. additioncontaining formic acid (0.05%) as the eluents, and analysis of the fractions by electrospray mass spectroscopy

Sources & evidence

ORD record
ord-a77f57331b13420d90bd992ce1d61e24
Source dataset
uspto-grants-2007_08
Patent number
US07259163B2

Reaction notes

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