Chlorotrimethylsilane → Methyl 3-iodobenzoate

HRID 1637101Notes

Reaction equation

HRID 1637101 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].Cl[Si](C)(C)[CH3:13]>CO>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:13])=[O:6]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 120603-Iodobenzoic acid

Product 1

HCID 69258Methyl 3-iodobenzoateYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

3-Iodobenzoic acid (10.0 g, 40.3 mmol) was placed in dry methanol (50 mL) under an argon atmosphere and was treated with chlorotrimethylsilane (15.4 mL, 0.12 mol). After heating at 65° C. for 4 h, the mixture was cooled to room temperature and was concentrated in vacuo. The residue was partitioned between ethyl acetate (100 mL) and water, the organic phase was washed twice with water, was dried (Na2SO4) and was evaporated to provide the titled compound as a white solid (10.6 g, 100%).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. concentrationwas concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate (100 mL) and water
  4. washthe organic phase was washed twice with water
  5. dry with materialwas dried (Na2SO4)
  6. customwas evaporated

Sources & evidence

ORD record
ord-2a79cce5680d4806a31eb172b9d8e5ee
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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