Potassium Carbonate → 4-Methoxy-3-(4,4,4-trifluoro-butoxy)-benzoic acid ethyl ester

HRID 1158472Notes

Reaction equation

HRID 1158472 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([OH:13])[CH:6]=1)[CH3:2].Br[CH2:16][CH2:17][CH2:18][C:19]([F:22])([F:21])[F:20].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH2:16][CH2:17][CH2:18][C:19]([F:22])([F:21])[F:20])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 15480330Ethyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 686174804-Methoxy-3-(4,4,4-trifluoro-butoxy)-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3-hydroxy-4-methoxy-benzoic acid ethyl ester (1.00 g, 5.10 mmol), 1-bromo-4,4,4-trifluorobutane (1.12 g, 5.86 mmol) and anhydrous K2CO3 (2.14 g, 15.3 mmol) in MeCN (10 mL) is refluxed with stirring overnight. After cooling, the mixture is filtered, and the filtrates are evaporated to drying to give the title compound as white solid. TLC, Rf (hexane/AcOEt 1:1)=0.62. MS: 307.0 [M+H]+. 1H-NMR (CDCl3): δ 1.42 (m, 3H), 2.1-2. (m, 2H), 2.3-2.45 (m, 2H), 3.95 (s, 3H), 4.14 (m, 2H), 4.39 (m, 2H), 6.93 (dd, 1H), 7.58 (d, 1H), 7.74 (dd, 1H) ppm.

Workup

  1. temperatureis refluxed
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. customthe filtrates are evaporated
  5. customto drying

Sources & evidence

ORD record
ord-797d690fb48147d99579496445433fe9
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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