Toluene → 6-(2,5-Difluorophenyl)nicotinic acid

HRID 602095Notes

Reaction equation

HRID 602095 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:21]=[CH:20][C:12]([C:13]([O:15]C(C)(C)C)=[O:14])=[CH:11][N:10]=1.C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:21]=[CH:20][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 67267400Tert-butyl 6-(2,5-difluorophenyl)nicotinate

Product 1

HCID 247299846-(2,5-Difluorophenyl)nicotinic acidYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 6-(2,5-difluorophenyl)nicotinate in DCM (12 mL) at 0° C. was added TFA (5 mL). After stirring at room temperature overnight, toluene was added (10 mL) and the solvent removed to give a white solid (176 mg, 97%), 6-(2,5-difluorophenyl)nicotinic acid. LC/MS (M+H)=236.0 observed, 236.05 expected

Workup

  1. customthe solvent removed

Sources & evidence

ORD record
ord-9bf8c0e5796c4a6a877aa5376e4af6bd
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Reaction notes

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