Methyl 2-chloro-4-vinylbenzoate → Methyl 2-chloro-4-ethylbenzoate

HRID 514543Notes

Reaction equation

HRID 514543 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]=[CH2:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>[O-]S([O-])(=O)=O.[Ba+2].[Pd].C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 57461224Methyl 2-chloro-4-vinylbenzoate

Product 1

HCID 82637044Methyl 2-chloro-4-ethylbenzoateYield 96%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Charged methyl 2-chloro-4-ethenylbenzoate (437 mg, 2.23 mmol), BaSO4/Pd (100 mg, 5%) and ethyl acetate (9 mL) to a flask, the mixture was then purged with H2, and stirred at room temperature for 4 h. The reaction mixture was then filtered, concentrated to give 424 mg of the title compound (96%). 1H NMR (400 MHz, CDCl3): δ 1.24 (3H, t, J=7.6 Hz), 2.65 (2H, q, J=7.6 Hz), 3.91 (3H, s), 7.12 (1H, dd, J=1.2 Hz, 8.4 Hz), 7.28 (1H, d, J=1.6 Hz), 7.77 (1H, d, J=8.0 Hz).

Workup

  1. customthe mixture was then purged with H2
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ab65ae4b91194545a96bfa08f292e48e
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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