Trifluoroacetic acid → HCID 86675146, compound

HRID 1503512Notes

Reaction equation

HRID 1503512 reaction equation
[Br:1][C:2]1[CH:18]=[C:17](/[CH:19]=[CH:20]/[CH:21]([C:26]2[CH:31]=[C:30]([Cl:32])[C:29]([Cl:33])=[C:28]([Cl:34])[CH:27]=2)[C:22]([F:25])([F:24])[F:23])[CH:16]=[CH:15][C:3]=1[C:4]([NH:6][CH2:7][C:8]([O:10]C(C)(C)C)=[O:9])=[O:5].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:18]=[C:17](/[CH:19]=[CH:20]/[CH:21]([C:26]2[CH:31]=[C:30]([Cl:32])[C:29]([Cl:33])=[C:28]([Cl:34])[CH:27]=2)[C:22]([F:24])([F:25])[F:23])[CH:16]=[CH:15][C:3]=1[C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86675147HCID 86675147, compound

Product 1

HCID 86675146HCID 86675146, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (E)-tert-butyl 2-(2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzamido)acetate (440 mg, 0.734 mmol) in DCM (36.0 ml), was added TFA (4.0 mL) and the reaction mixture was stirred at RT for 1 h. The reaction mixture was concentrated under reduced pressure to obtain residue which was washed with n-pentane to afford the title compound as an off-white solid (310 mg, 78%): 1H NMR (400 MHz, CDCl3) δ 13.0 (s, 1H), 8.75 (t, J=5.7 Hz, 1H), 7.93 (m, 2H), 7.62 (d, J=7.5 Hz, 1H), 7.40 (d, J=8.1 Hz, 1H), 6.96 (dd, J=15.3, 9.3 Hz, 1H), 6.78 (d, J=15.3 Hz, 1H), 4.83 (m, 1H), 3.90 (d, J=5.7 Hz, 2H); ESIMS m/z 543.61 ([M+H]+); IR (thin film) 3429, 1635, 1114, 772 cm−1.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto obtain residue which
  3. washwas washed with n-pentane

Sources & evidence

ORD record
ord-4fea9c6a5eeb429e863a9a05d3b437e6
Source dataset
uspto-grants-2015_12
Patent number
US09212163B2

Reaction notes

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