Methyl 5-chloro-2-ethynylbenzoate → Methyl 5-chloro-2-ethylbenzoate

HRID 1959288Notes

Reaction equation

HRID 1959288 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]#[CH:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 86672667Methyl 5-chloro-2-ethynylbenzoate

Product 1

HCID 59382453Methyl 5-chloro-2-ethylbenzoateYield 93.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 5-chloro-2-ethynylbenzoate (5.34 g, 27.44 mmol) in Ethyl acetate (135 ml) was added Pd/C (10%) (50% water, 2.92 g, 1.37 mmol). The reaction mixture was stirred under a hydrogen atmosphere at room temperature for 3 hours. LCMS indicated the reaction had gone to completion and the mixture was filtered through Celite. The filter cake washed with EtOAc (50 ml) and the filtrate was concentrated under reduced pressure to give 5.12 g (93.9%) of methyl 5-chloro-2-ethylbenzoate as a brown oil which was suitable for use without any further purification. LC-MS 56%, 2.21 min (3 minute LC-MS method), m/z=198.9/200.9, 1H NMR (500 MHz, Chloroform-d) δ ppm 7.84 (d, J=2.3 Hz, 1H), 7.39 (dd, J=8.3, 2.3 Hz, 1H), 7.21 (d, J=8.3 Hz, 1H), 3.90 (s, 3H), 2.94 (q, J=7.5 Hz, 2H), 1.21 (t, J=7.5 Hz, 3H).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. washThe filter cake washed with EtOAc (50 ml)
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-909b848e54884da0894167fcd8c4756f
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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