tert-butyl 4-((E)-2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)vinyl)-2-(4-fluoroanilino)benzoate → 4-((E)-2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)vinyl)-2-(4-fluoroanilino)benzoic acid

HRID 2191726Notes

Reaction equation

HRID 2191726 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9](/[CH:11]=[CH:12]/[C:13]3[CH:25]=[CH:24][C:16]([C:17]([O:19]C(C)(C)C)=[O:18])=[C:15]([NH:26][C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[CH:14]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1>FC(F)(F)C(O)=O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9](/[CH:11]=[CH:12]/[C:13]3[CH:25]=[CH:24][C:16]([C:17]([OH:19])=[O:18])=[C:15]([NH:26][C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[CH:14]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 68963963tert-butyl 4-((E)-2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)vinyl)-2-(4-fluoroanilino)benzoate

Product 1

HCID 576681064-((E)-2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)vinyl)-2-(4-fluoroanilino)benzoic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid 10 mL solution of the obtained tert-butyl 4-((E)-2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)vinyl)-2-(4-fluoroanilino)benzoate was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure to give 4-((E)-2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)vinyl)-2-(4-fluoroanilino)benzoic acid 17 mg of pale yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-729e3599879f43829350a26b529c3790
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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