Dimethylformamide → (4-Chlorocarbonyl-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester

HRID 1929577Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:8]([CH3:15])=[C:9]2[C:12](O)=[O:13])=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:24])=O.CN(C)C=O>O1CCCC1>[CH3:20][O:19][C:17](=[O:18])[CH2:16][C:7]1[C:8]([CH3:15])=[C:9]([C:12]([Cl:24])=[O:13])[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=2)[CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 7-fluoro-3-methoxycarbonylmethyl-2-methyl-naphthalene-1-carboxylic acid (500 mg, 1.81 mmol) in anhydrous tetrahydrofuran (10 mL), was added oxalyl chloride (250 μL) and N,N-dimethylformamide (30 μL). The resulting mixture was stirred at 60° C. for 2 hours, and concentrated in vacuo to afford (4-chlorocarbonyl-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (526 mg, 99%) as a light yellow solid, which was used in the next step without further purification.

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e99bcebf8fcf48ac9459c51f86b45e83
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188090B2

Reaction notes

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