Ethyl bromoacetate → Ethyl 2,6-bis(trifluoromethyl)-4-[(ethoxycarbonyl)methoxy]-5-methyl-3-pyridinecarboxylate

HRID 542135Notes

Reaction equation

HRID 542135 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([OH:14])[C:6]([CH3:15])=[C:5]([C:16]([F:19])([F:18])[F:17])[N:4]=1.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[F:21][C:2]([F:20])([F:1])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:14][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:6]([CH3:15])=[C:5]([C:16]([F:19])([F:18])[F:17])[N:4]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178469144HCID 178469144, compound

Product 1

HCID 13882924Ethyl 2,6-bis(trifluoromethyl)-4-[(ethoxycarbonyl)methoxy]-5-methyl-3-pyridinecarboxylateYield 70.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5.0 g (0.016 mol) of product of Example 35, 3.95 g (0.024 mol) of ethyl bromoacetate, 2.18 g (0.016 mol) of K2CO3 and 75 ml of acetone was held at reflux for 18 hours and filtered. The filtrate was concentrated. The residue was stirred with toluene and filtered. The toluene filtrate was concentrated to give 4.46 g (70.2%) of product as a solid; mp 42°-44° C.

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. filtrationfiltered
  5. concentrationThe toluene filtrate was concentrated

Sources & evidence

ORD record
ord-4c539e8c9af0443c9efce1a93aada99e
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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