Acetic Anhydride → (4-Acetoxy-6-fluoro-3-iodo-naphthalen-2-yl)acetic acid methyl ester

HRID 238640Notes

Reaction equation

HRID 238640 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]([I:15])=[C:13]([OH:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=2)[CH:6]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.Cl>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]([I:15])=[C:13]([O:16][C:19](=[O:21])[CH3:20])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=2)[CH:6]=1

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 59326608(6-Fluoro-4-hydroxy-3-iodo-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 59326600(4-Acetoxy-6-fluoro-3-iodo-naphthalen-2-yl)acetic acid methyl esterYield 53.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

To a stirred solution of (6-fluoro-4-hydroxy-3-iodo-naphthalen-2-yl)-acetic acid methyl ester (500 mg, 1.4 mmol) and 4-dimethylaminopyridine (34 mg, 0.28 mmol) in pyridine (3 mL) was added acetic anhydride (160 μL, 1.7 mmol). After being stirred at room temperature overnight, the resulting mixture was diluted with 10% hydrochloric acid (20 mL), and extracted with ethyl acetate (30 mL×2). The combined organic layers were washed with brine (30 mL×2), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column (elution with 20% ethyl acetate in petroleum ether) to afford (4-acetoxy-6-fluoro-3-iodo-naphthalen-2-yl)acetic acid methyl ester (300 mg, 53%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (30 mL×2)
  2. washThe combined organic layers were washed with brine (30 mL×2)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column (elution with 20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-e7e184dd6ee14ab4acf86753c795b498
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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