2,2-Difluoroethan-1-ol → 2-(2,2-Difluoroethyl)oxy-5-nitro-nicotinic acid

HRID 1846089Notes

Reaction equation

HRID 1846089 reaction equation
Cl[C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:14][CH:15]([F:18])[CH2:16][OH:17].CC([O-])(C)C.[K+].C(Cl)Cl.CCO>C1COCC1>[F:14][CH:15]([F:18])[CH2:16][O:17][C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 1361872,2-Difluoroethan-1-olHCID 125426642-Chloro-5-nitropyridine-3-carboxylic acidHCID 21584144Dichloromethane ethanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 866586692-(2,2-Difluoroethyl)oxy-5-nitro-nicotinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 5a from 2 chloro-5-nitro nicotinic acid and 2,2-difluoroethanol with KOtBu in THF. Yield: (25%). MS [M−H]−=247; TLC: Rf=0.13 (silica gel, DCM:EtOH 9:1).

Sources & evidence

ORD record
ord-452cab8c4fac48359adc1ae88ceaf743
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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