Methanol → Methyl 3-iodobenzoate

HRID 2421649Notes

Reaction equation

HRID 2421649 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:15]O>>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:15])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 120603-Iodobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 69258Methyl 3-iodobenzoateYield 93%

Procedure

3-iodobenzoic acid (7.44 g, 30 mmol) was suspended in dry MeOH (40 mL) under nitrogen at 0° C. SOCl2 (3.3 mL) was added over 5 minutes. Stirring continued at room temperature for 16 hours, after which the reaction mixture was concentrated. The residue was dissolved in EtOAc and was washed twice with NaHCO3 (conc.). The organic solution was dried over MgSO4, filtered and concentrated to yield a white crystalline solid (7.32 g, 93%). NMR 1H (ppm, CDCl3): 8.36 (t, J4=1.6 Hz, 1H), 7.98 (d, J3=7.8 Hz, 1H), 7.86 (d, J3=7.9 Hz, 1H), 7.16 (t, J3=7.8 Hz, 1H), 3.90 (s, 3H).

Workup

  1. concentrationafter which the reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwas washed twice with NaHCO3 (conc.)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c5a9e382ed2d4f3080a75b3380c82c0c
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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