Iodine → Ethyl 5-iodo-2-methylbenzoate

HRID 1767207Notes

Reaction equation

HRID 1767207 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9](N)[CH:8]=[CH:7][C:6]=1[CH3:12])[CH3:2].[I:14]I.N(OC(C)(C)C)=O>C1(C)C=CC=CC=1>[CH3:9][CH2:10][CH2:5][CH:6]([CH3:12])[CH3:7].[CH3:2][CH2:1][O:3][C:4]([CH3:5])=[O:13].[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([I:14])[CH:8]=[CH:7][C:6]=1[CH3:12])[CH3:2]

Participants

6

Reactant 3

HCID 807IodineHCID 10906Tert-Butyl nitriteHCID 18690998HCID 18690998, compound

Product 2

HCID 21882781Isohexane ethyl acetateHCID 44829046Ethyl 5-iodo-2-methylbenzoateYield 188.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-amino-2-methylbenzoic acid ethyl ester (500 mg, 2.8 mmol) and iodine (425 mg, 1.68 mmol) in toluene (20 ml) was cooled to 0° C. and treated with t-butyl nitrite (303 mg, 2.94 mmol). The reaction mixture was stirred at 0° C. for 1 hour then at room temperature over the weekend. The reaction mixture was washed with 10% aq sodium thiosulphate (20 ml), and brine (20 ml), dried and evaporated. Flash chromatography [silica, iso-hexane/EtOAc, 9:1] gave 5-iodo-2-methylbenzoic acid ethyl ester as a brown oil 510 mg 63%. 1H NMR (CDCl3):1.39 (3H, t, J=12 Hz), 2.53 (3H, s), 4.36 (2H, q, J=12 Hz), 6.97 (1H,d, J=12 Hz), 7.37 (1H, d, J=12 Hz), 8.20 (1H, s).

Workup

  1. customat room temperature
  2. washThe reaction mixture was washed with 10% aq sodium thiosulphate (20 ml), and brine (20 ml)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-977eb23fa6dd4421912dce89687d1884
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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