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

HRID 2208860Notes

Reaction equation

HRID 2208860 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 95.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 5-chloro-2-ethynylbenzoate (5.34 g, 27 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. 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 (94%) of the title compound as a brown oil which was suitable for use without any further purification. LC-MS 56%, 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-1cd2925534d34313a176ac03e14b8896
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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