Iodine → Methyl 2-hydroxy-5-iodo-3-methylbenzoate

HRID 1805910Notes

Reaction equation

HRID 1805910 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[I:13]I>CO.S([O-])([O-])(=O)=O.[Ag+2]>[OH:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([I:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 807IodineHCID 31835Benzoic acid, 2-hydroxy-3-methyl-, methyl ester

Product 1

HCID 14172484Methyl 2-hydroxy-5-iodo-3-methylbenzoate

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-hydroxy-3-methylbenzoate (0.869 g, 5.23 mmol) in MeOH (5 mL) was added dropwise to a suspension of iodine (1.327 g, 5.23 mmol) and silver sulfate (1.63 g, 5.23 mmol), at room temperature under N2. The resultant brown suspension was stirred for 3 h after which time a colorless suspension was observed. The mixture was filtered through a plug of Celite, washed with MeOH (30 mL) and concentrated in vacuo to afford methyl 2-hydroxy-5-iodo-3-methylbenzoate, as a colorless solid. LCMS calc.=292.1; found=292.7 (M+H)+. 1H NMR (500 MHz, CHCl3): δ 11.0 (s, 1 H); 8.02 (s, 1 H); 7.62 (s, 1 H); 3.97 (s, 3 H); 2.25 (s, 3 H).

Workup

  1. filtrationThe mixture was filtered through a plug of Celite
  2. washwashed with MeOH (30 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec589faa79af48cbb226388831828a29
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

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