Iodine → Ethyl 3-(2-iodo-5-methoxyphenyl)propionate

HRID 1496827Notes

Reaction equation

HRID 1496827 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1.[I:16]I.C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC>C(#N)C>[I:16][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 807IodineHCID 159629ButyltriphenylphosphoniumHCID 584318Ethyl 3-(3-methoxyphenyl)propanoate

Product 1

HCID 11110409Ethyl 3-(2-iodo-5-methoxyphenyl)propionateYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ester 25 (1.618 g, 7.77 mmol) in acetonitrile (100 mL), iodine (1.972 g, 7.77 mmol) and n-butyltriphenylphosphonium peroxodisulfate (6.455 g, 7.77 mmol) were added and refluxed for 45 min. The reaction mixture was cooled to room temperature and the excess of iodine was removed by dropwise addition of 1M Na2S2O3 solution. The colourless solution was transferred to a separatory funnel and the organic layer was separated and dried over Na2SO4. Evaporation of the solvent followed by means of column chromatography on silica gel (hexane/isopropylether 10:1) gave 1.982 mg of iodinated ester 26 as a yellowish oil. Yield 76%. 1H NMR (300 MHz, CDCl3) δ ppm: 7.65 (d, J=8.7 Hz, 1H), 6.82 (d, J=3.0 Hz, 1H), 6.51 (dd, J1=8.7 Hz, J2=3.0 Hz, 1H), 4.14 (q, J=7.1 Hz, 2H), 3.76 (s, 3H), 3.00 (t, J=7.9 Hz, 2H), 2.60 (t, J=7.9 Hz, 2H), 1.25 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ ppm: 172.4, 160.0, 144.0, 139.9, 115.5, 114.1, 88.6, 60.5, 55.3, 35.9, 34.4, 14.2; HRMS (EI) m/z: calcd for C12H15IO3: 334.0065. found: 334.0082.

Workup

  1. temperaturerefluxed for 45 min
  2. customthe excess of iodine was removed by dropwise addition of 1M Na2S2O3 solution
  3. customThe colourless solution was transferred to a separatory funnel
  4. customthe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e423de8dc68e41888bf6bbd5e43f0e27
Source dataset
uspto-grants-2015_12
Patent number
US09199936B2

Reaction notes

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