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

HRID 1929577
Notes
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Reaction equation

HRID 1929577 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 593267347-Fluoro-3-methoxycarbonylmethyl-2-methyl-naphthalene-1-carboxylic acid

Product 1

HCID 59326710(4-Chlorocarbonyl-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

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

  1. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes