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

HRID 2208888Notes

Reaction equation

HRID 2208888 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]>CC(OC)(C)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 93.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of methyl 5-chloro-2-ethynylbenzoate (1.13 g, 5.8 mmol) in TBME (50 ml) was added Pd/C (10%) (50% water, 0.61 g, 0.29 mmol). The reaction mixture was stirred under a hydrogen atmosphere for 130 minutes. The mixture was filtered through Celite and the filter cake was washed with TBME. The filtrate was concentrated in-vacuo to give the title compound (1.08 g, 74%) as a pale brown oil. LC-MS 79%, m/z=198.9/200.9; 1H NMR (500 MHz, Chloroform-d) δ ppm 7.85 (s, 1H) 7.40 (d, J=8.20 Hz, 1H) 7.22 (d, J=8.20 Hz, 1H) 3.91 (s, 3H) 2.95 (q, J=7.46 Hz, 2H) 1.22 (t, J=7.49 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed with TBME
  3. concentrationThe filtrate was concentrated in-vacuo

Sources & evidence

ORD record
ord-0baace02c7f340dc9351b15dffc20141
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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