N-Iodosuccinimide → (6-Fluoro-4-hydroxy-3-iodo-naphthalen-2-yl)-acetic acid methyl ester

HRID 238639Notes

Reaction equation

HRID 238639 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[CH:11]=2)[CH:6]=1.[I:18]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.S(=O)(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[C:14]([I:18])=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[CH:11]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 20335012(6-Fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 59326608(6-Fluoro-4-hydroxy-3-iodo-naphthalen-2-yl)-acetic acid methyl esterYield 54%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516919Sodium BisulfateSolvent

Procedure

To a solution of (6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (600 mg, 2.56 mmol, the product of 8th step for example 1-1) in chloroform (260 mL) was added N-iodosuccinimide (577 mg, 2.56 mmol) at 0° C. The mixture was allowed to warm to room temperature and stirred at room temperature for 2 hours. The resulting mixture was diluted with 10% aqueous solution of sodium bisulfate (100 mL). The organic layer was separated, washed with brine (100 mL), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column (elution with 15% ethyl acetate in petroleum ether) to afford (6-fluoro-4-hydroxy-3-iodo-naphthalen-2-yl)-acetic acid methyl ester (500 mg, 54%) as a white solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (100 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column (elution with 15% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-bcb6350085cd46b88e6c9115c5f3eedd
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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