tert-Butanol → Tert-butyl 3-iodo-2-methoxybenzoate

HRID 1486182Notes

Reaction equation

HRID 1486182 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[I:11][C:12]1[C:13]([O:21][CH3:22])=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](Cl)=[O:16]>C1COCC1>[I:11][C:12]1[C:13]([O:21][CH3:22])=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:16]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 867229723-Iodo-2-methoxy-benzoyl chlorideHCID 178418339Butyllithium

Product 1

HCID 86722973Tert-butyl 3-iodo-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (−5° C.) solution of tert-butanol (12.87 mL, 30 mmol) in THF (30 mL) was added, dropwise, BuLi (12.0 mL, 2.5 M in hexanes, 30 mmol). On complete addition, the solution was stirred for 20 minutes. To this solution is added a solution of 3-Iodo-2-methoxy-benzoyl Chloride (8.8 g, 29.8 mmol) in THF (12 mL). On complete addition, the cold bath was removed and stirring continued for 1.5 hours. This solution was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by silica chromatography (50 g silica; eluted with 0-20% ethyl acetate in hexanes) to give the title compound as an oil.

Workup

  1. additionwas added
  2. additionOn complete addition
  3. additionOn complete addition
  4. customthe cold bath was removed
  5. stirringstirring
  6. waitcontinued for 1.5 hours
  7. additionThis solution was diluted with ethyl acetate
  8. washwashed with water and brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica chromatography (50 g silica; eluted with 0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5834b9497bb740be9637de8c89956c4d
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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