4-Bromo-2-ethenyl-1-fluorobenzene → 4-Bromo-2-ethyl-1-fluorobenzene

HRID 1515565Notes

Reaction equation

HRID 1515565 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH:9]=[CH2:10])[CH:3]=1.[H][H]>CCOC(C)=O.[Pd]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH2:9][CH3:10])[CH:3]=1

Participants

5

Reactant 2

HCID 219339834-Bromo-2-ethenyl-1-fluorobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 226410254-Bromo-2-ethyl-1-fluorobenzeneYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromo-1-fluoro-2-vinylbenzene (470 mg) was hydrogenated in EtOAc with 10% Pd/C (100 mg) with a hydrogen balloon for 2.0 h. The Pd/C was removed by filtration. The filtrate was condensed to give 95A (290 mg, 62% yield) as an orange oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.22 (t, J=6.81 Hz, 3H) 2.63 (d, J=7.03 Hz, 2H) 6.88 (t, J=8.57 Hz, 1H) 7.25 (s, 1H) 7.32 (d, J=4.39 Hz, 1H).

Workup

  1. customThe Pd/C was removed by filtration
  2. customcondensed

Sources & evidence

ORD record
ord-d5e91bbeeaa241e8854949b9001d98f9
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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