Trifluoroacetic acid → 3-Aminomethyl-5-chloro-4-fluoro-benzonitrile

HRID 1527475Notes

Reaction equation

HRID 1527475 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([C:15]#[N:16])[CH:12]=[C:11]([Cl:17])[C:10]=1[F:18])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]1[CH:14]=[C:13]([CH:12]=[C:11]([Cl:17])[C:10]=1[F:18])[C:15]#[N:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68283962(3-Chloro-5-cyano-2-fluoro-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 682834833-Aminomethyl-5-chloro-4-fluoro-benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-chloro-5-cyano-2-fluoro-benzyl)-carbamic acid tert-butyl ester (645 mg, 2.27 mmol) in CH2Cl2 (15 mL) was added TFA (1.75 mL, 22.7 mmol), and stirring was continued at RT overnight. Volatiles were removed under reduce pressure, water was added and the mixture was washed with EtOAc. The aqueous layer was basified to pH=12 by addition of 4M NaOH solution and extracted twice with EtOAc. The combined organics were dried (phase separator) and evaporated to afford the title compound as a beige solid. MS (LC/MS): 185.0 [M+H]+; tR (HPLC conditions c): 2.62 min.

Workup

  1. customVolatiles were removed
  2. additionwas added
  3. washthe mixture was washed with EtOAc
  4. additionThe aqueous layer was basified to pH=12 by addition of 4M NaOH solution
  5. extractionextracted twice with EtOAc
  6. customThe combined organics were dried (phase separator)
  7. customevaporated

Sources & evidence

ORD record
ord-7ae8cd0958a2440cac83ab203cc94379
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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