HCID 59006697, compound → Benzene, 2-ethynyl-1,4-difluoro-

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Reaction Conditions

Reaction Steps

The title compound of Example 37.1 (10.2 g, 48.7 mmol) was dissolved in dry THF (63 mL), cooled on a dry ice/isopropanol bath to −55° C. and butyl lithium (2.5 M, 42 mL, 105 mmol) was added within 30 min at a rate that kept the temperature below −40° C. LC/MS showed good conversion 20 min after the addition of BuLi and stirring. The mixture was warmed up to 0° C. with the aid of a water bath. At 0° C. the mixture was quenched with potassium hydrogen sulfate (2 M solution) until a neutral aqueous phase was achieved. Diethyl ether was added and the water phase was extracted twice with a small amount of diethyl ether. The organic phases were combined and dried (MgSO4), filtered and carefully evaporated using only heat. The solvent was removed by distillation under normal air pressure with the oil bath temperature at 80° C. The remaining residue was distilled in vacuo, and the fraction at 30° C./0 mmHg was collected. Yield 51%, 3.8 g.

Provenance & Evidence