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

HRID 1054130Notes

Reaction equation

HRID 1054130 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, 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-f26e720174874bacbeb0bc6fb2e4ffd6
Source dataset
uspto-grants-2016_07
Patent number
US09394276B2

Reaction notes

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