Carbon Dioxide → Lithium 4-chloro-5-fluoro-2-(methoxymethoxy)benzoate

HRID 225457

Reaction equation

HRID 225457 reaction equation
C([Li:5])CCC.Br[C:7]1[CH:12]=[C:11]([F:13])[C:10]([Cl:14])=[CH:9][C:8]=1[O:15][CH2:16][O:17][CH3:18].[C:19](=[O:21])=[O:20]>C(OCC)C>[Cl:14][C:10]1[C:11]([F:13])=[CH:12][C:7]([C:19]([O-:21])=[O:20])=[C:8]([O:15][CH2:16][O:17][CH3:18])[CH:9]=1.[Li+:5]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 542631541-Bromo-4-chloro-5-fluoro-2-(methoxymethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 69077744Lithium 4-chloro-5-fluoro-2-(methoxymethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-butyllithium was added to a diethyl ether solution of 1-bromo-4-chloro-5-fluoro-2-(methoxymethoxy)benzene in a dry ice-acetone bath and stirred for one hour. The reaction solution was added to a mixture of dry ice and diethyl ether and stirred for two hours to give lithium 4-chloro-5-fluoro-2-(methoxymethoxy)benzoate. Phosphorus oxychloride was added to a mixture of the obtained lithium 4-chloro-5-fluoro-2-(methoxymethoxy)benzoate, 3-aminothiophene-2-carboxamide and pyridine in a MeOH ice bath and stirred for one hour to give 3-{[4-chloro-5-fluoro-2-(methoxymethoxy)benzoyl]amino}thiophene-2-carboxamide.

Workup

  1. stirringstirred for two hours

Sources & evidence

ORD record
ord-6ea577ad934e49d293cc93832ebd8a2d
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Linked notes

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