HCID 90310750, compound → HCID 90310844, compound

HRID 1519174Notes

Reaction equation

HRID 1519174 reaction equation
[C:1]([Si:5]([O:8][C:9]1[C:14]([CH:15]=[CH2:16])=[CH:13][CH:12]=[CH:11][C:10]=1[F:17])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([Si:5]([O:8][C:9]1[C:10]([F:17])=[CH:11][CH:12]=[CH:13][C:14]=1[CH2:15][CH3:16])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 90310750HCID 90310750, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 90310844HCID 90310844, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of tert-butyl(2-fluoro-6-vinylphenoxy)dimethylsilane (1.18 g, 4.67 mmol) in ethyl acetate (61 mL) under nitrogen, was added 497 mg of 10% palladium on carbon. The flask was then equipped with a hydrogen containing balloon and the reaction mixture stirred rapidly for 4 hours. The hydrogen balloon was removed, the reaction mixture sparged with nitrogen, and then filtered through a plug of Celite®, eluting with EtOAc. The filtrate was concentrated to dryness to afford the title compound that was used without further purification. 1H NMR (500 MHz, CDCl3) δ 6.94-6.85 (m, 2H), 6.85-6.77 (m, 1H), 2.65 (q, J=7.6, 2H), 1.19 (t, J=7.5, 3H), 1.02 (s, 9H), 0.21 (d, J=2.7, 6H).

Workup

  1. customThe hydrogen balloon was removed
  2. customthe reaction mixture sparged with nitrogen
  3. filtrationfiltered through a plug of Celite®
  4. washeluting with EtOAc
  5. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-e86bb1ff989440a09fca8459b20d09c6
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

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