1-Iodo-4-(trifluoromethoxy)benzene → 2,2-Dimethyl-5-(4-trifluoromethoxy-phenyl)-pent-4-yn-1-ol

Temperatur

50 °C

A mixture of 1-iodo-4-trifluoromethoxy-benzene (3.56 g, 12 mmol), Pd(PPh3)4 (578 mg, 0.5 mmol) and cuprous iodide (95 mg, 0.5 mmol) in piperidine (40 ml) was degassed (Ar) and stirred for 30 min at 50° C. under an argon atmosphere. 2,2-Dimethyl-pent-4-yn-1-ol (1.25 g, 10 mmol, 90% purity) [Magnus, Philip; Slater, Martin J.; Principe, Lawrence M. Journal of Organic Chemistry (1989), 54(21), 5148-5153] in piperidine (20 ml) was added within 60 min at 50° C. During the addition the oil bath temperature was slowly raised to 80° C. starting after 30 min. The mixture was stirred for 2 h at this temperature. The reaction mixture was cooled to ambient temperature, poured into a solution of aqueous 10% KHSO4/ice water 1/1 and extracted two times with ether. The combined extracts were washed with aqueous 10% KHSO4 and aqueous 10% NaCl and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography (silica gel, heptane/AcOEt 2:1 to 1:1) to give 1.91 g (7 mmol, 70%) of the title compound as yellow oil.

1. customwas degassed (Ar)
2. additionDuring the addition the oil bath temperature
3. temperaturewas slowly raised to 80° C.
4. waitstarting after 30 min
5. stirringThe mixture was stirred for 2 h at this temperature
6. temperatureThe reaction mixture was cooled to ambient temperature
7. extractionextracted two times with ether
8. washThe combined extracts were washed with aqueous 10% KHSO4 and aqueous 10% NaCl
9. dry with materialdried over sodium sulfate
10. customThe solvent was removed under reduced pressure
11. customthe residue purified by flash chromatography (silica gel, heptane/AcOEt 2:1 to 1:1)

ORD-Eintrag

ord-0be0ed9b15a4445e94837d96637fad07

Quelldatensatz

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07405236B2