Trifluoroacetic acid → HCID 66743652, compound

HRID 1054132Notes

Reaction equation

HRID 1054132 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:17]([F:19])[F:18])=[C:6](/[CH:8]=[CH:9]/[C:10]([O:12]C(C)(C)C)=[O:11])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:17]([F:18])[F:19])=[C:6](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736321(E)-tert-Butyl 3-(5-chloro-2-(difluoromethyl)phenyl)acrylate

Product 1

HCID 66743652HCID 66743652, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 14B (232 mg, 0.804 mmol) in DCM (2.0 mL) was added TFA (2.0 mL, 26.0 mmol). The reaction was stirred under argon at rt. After 1 h, the solvent was removed and residue was dried to give Intermediate 14 (191 mg, 100%) as tan solid. 1H NMR (400 MHz, MeOD) δ 7.99 (dt, J=15.8, 1.5 Hz, 1H), 7.83 (s, 1H), 7.60 (d, J=8.3 Hz, 1H), 7.55-7.48 (m, 1H), 7.01 (t, J=54.6 Hz, 1H), 6.51 (d, J=15.8 Hz, 1H). 19F NMR (376 MHz, MEOD) δ −111.67 (s, 2F) ppm. MS (ESI) m/z: 233.1 (M+H)+.

Workup

  1. customthe solvent was removed
  2. customresidue was dried

Sources & evidence

ORD record
ord-3a63270f3e81466baaddb87f9dd2ee52
Source dataset
uspto-grants-2016_07
Patent number
US09394276B2

Reaction notes

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