(E)-tert-Butyl 3-(6-acetyl-3-chloro-2-fluorophenyl)acrylate → HCID 66698622, compound

HRID 515765Notes

Reaction equation

HRID 515765 reaction equation
[C:1]([C:4]1[C:9](/[CH:10]=[CH:11]/[C:12]([O:14]C(C)(C)C)=[O:13])=[C:8]([F:19])[C:7]([Cl:20])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:1]([C:4]1[C:9](/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])=[C:8]([F:19])[C:7]([Cl:20])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 66698573(E)-tert-Butyl 3-(6-acetyl-3-chloro-2-fluorophenyl)acrylate

Product 1

HCID 66698622HCID 66698622, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Intermediate 12D (25 g, 84 mmol) in DCM (330 mL) and TFA (330 mL) was stirred at rt. After 1.5 h, the solvent was concentrated to give Intermediate 12 (19.5 g, 97.0% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 12.69 (bs, 1 H), 7.80-7.76 (m, 2 H), 7.62 (d, J=12.1 Hz, 1 H), 6.30 (dd, J=2.4, 2.0 Hz, 1 H), 2.6 (s, 3H) ppm. MS (ESI) m/z: 241 (M−H)+.

Workup

  1. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-7c35282619ad48748d4a4261a479216a
Source dataset
uspto-grants-2015_08
Patent number
US09108951B2

Reaction notes

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