Trifluoroacetic acid → 4-Amino-5-chloro-2-fluorobenzoic acid

HRID 2234450Notes

Reaction equation

HRID 2234450 reaction equation
C([O:5][C:6](=[O:16])[C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([NH2:14])=[CH:9][C:8]=1[F:15])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:14][C:10]1[C:11]([Cl:13])=[CH:12][C:7]([C:6]([OH:16])=[O:5])=[C:8]([F:15])[CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68684306Tert-butyl 4-amino-5-chloro-2-fluorobenzoate2×

Product 1

HCID 686839334-Amino-5-chloro-2-fluorobenzoic acidYield 105.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-5-chloro-2-fluorobenzoic acid tert-butyl ester (Intermediate 177; 3.0 g, 12.21 mmol) was dissolved in DCM (75 mL) and trifluoroacetic acid (25 mL) added. The mixture was stirred for 1 hour at room temperature and then concentrated to yield the title compound as a pale yellow solid (2.45 g, 100%).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-2da3fecb0778402494c1e84b9da10a2b
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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