Sodium Trifluoroacetate → 1-Naphthalenecarboxylic acid, 6-methoxy-5-(trifluoromethyl)-, methyl ester

HRID 1383122Notes

Reaction equation

HRID 1383122 reaction equation
[CH3:1][O:2][C:3]1[C:4](Br)=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=[CH:6]2.[F:18][C:19]([F:24])([F:23])C([O-])=O.[Na+]>[Cu]I.CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([C:19]([F:24])([F:23])[F:18])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=[CH:6]2

Participants

5

Reactant 2

HCID 517019Sodium Trifluoroacetate2×HCID 109352981-Naphthalenecarboxylic acid, 5-bromo-6-methoxy-, methyl ester

Product 1

HCID 136041041-Naphthalenecarboxylic acid, 6-methoxy-5-(trifluoromethyl)-, methyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

Using the same general procedure as in Comparative Example A, one molar proportion of methyl 6-methoxy-5-bromo-1-naphthoate (MMBN) was reacted with 1.7 molar proportions of sodium trifluoroacetate in the presence of 2 molar proportions of CuI and molar proportions of N,N-dimethylformamide (DMF), with an additional 0.95 molar proportion of sodium trifluoroacetate being added during the course of the reaction. The total reaction time was 5 hours. After workup, the desired methyl 6-methoxy-5-trifluoromethyl-1-naphthoate (MMTN) was isolated in a 76% yield.

Workup

  1. additionadded during the course of the reaction

Sources & evidence

ORD record
ord-791f6f985e9742caa72ea3420040184c
Source dataset
uspto-grants-1989_02
Patent number
US04808748

Reaction notes

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