Toluene → 6-(2-Fluorophenyl)nicotinic acid

HRID 602098

Reaction equation

HRID 602098 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:20]=[CH:19][C:11]([C:12]([O:14]C(C)(C)C)=[O:13])=[CH:10][N:9]=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][CH:5]=[CH:4][C:3]=1[C:8]1[CH:20]=[CH:19][C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 67267995Tert-butyl 6-(2-fluorophenyl)nicotinate

Product 1

HCID 247299716-(2-Fluorophenyl)nicotinic acidYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 6-(2-fluorophenyl)nicotinate (479 mg, 1.75 mmol) in DCM (12 mL) at 0° C. was added TFA (2.5 mL). After stirring at rt overnight, toluene was added (10 mL) and the solvent removed to give a white solid (375 mg, 98%), 6-(2-fluorophenyl)nicotinic acid. LC/MS (M+H)=218.0 observed, 218.06 expected.

Workup

  1. customthe solvent removed

Sources & evidence

ORD record
ord-e8914897738a41368082a8bb2d310a98
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Linked notes

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