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

HRID 716634Notes

Reaction equation

HRID 716634 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%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.69 (bs, 1H), 7.80-7.76 (m, 2H), 7.62 (d, J=12.1 Hz, 1H), 6.30 (dd, J=2.4, 2.0 Hz, 1H), 2.6 (s, 3H) ppm. MS (ESI) m/z: 241 (M−H)+.

Workup

  1. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-2f7dc0586c934a6b9b82129dfb9c5b94
Source dataset
uspto-grants-2015_11
Patent number
US09192607B2

Reaction notes

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