Trifluoroacetic acid → 3-Amino-4-fluoro-2-methylphenol

HRID 1771653Notes

Reaction equation

HRID 1771653 reaction equation
C(OC([N:8]([C:16]1[C:21]([F:22])=[CH:20][CH:19]=[C:18]([OH:23])[C:17]=1[CH3:24])C(=O)OC(C)(C)C)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:16]1[C:17]([CH3:24])=[C:18]([OH:23])[CH:19]=[CH:20][C:21]=1[F:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89444253Tert-butyl N-tert-butoxycarbonyl-N-(6-fluoro-3-hydroxy-2-methyl-phenyl)carbamate

Product 1

HCID 177757273-Amino-4-fluoro-2-methylphenolYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-tert-butoxycarbonyl-N-(6-fluoro-3-hydroxy-2-methyl-phenyl)carbamate (500 mg, 1.46 mmol, 1.0 eq) in DCM (6 mL) was added TFA (2 mL). The reaction was stirred at room temperature overnight, then the solvent was removed in vacuo, to give the title compound as yellow oil (200 mg, 97%).

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b73296abdbe340f0a353d8740f4865b5
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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