Water → HCID 68668443, compound

Temperature

70 °C

To a solution of the product from Step 2, ethyl 2-(4-bromo-3-methoxyphenyl)cyclohex-1-ene-1-carboxylate (2.0 g, 5.9 mmol) in THF (120 mL), EtOH (50 mL), and water (12 mL) was added LiOH (0.565 g, 23.6 mmol) and the reaction was stirred at 70° C. for 24 h. After cooling to r.t., the EtOH and THF were removed in vacuo and the aqueous layer was washed with Et2O. The pH was then adjusted to 1.4 with concentrated HCl and extracted with DCM two times. The organic layer was then dried over Na2SO4 and the solvent was removed in vacuo to yield 2-(4-bromo-3-methoxyphenyl)cyclohex-1-ene-1-carboxylic acid, which was dissolved in PhMe (9.6 mL) and treated with TEA (0.94 mL, 6.75 mmol) and diphenylphosphoryl azide (1.04 mL, 4.82 mmol). After 1 h at r.t., the mixture was filtered through a pad of silica washing with PhMe. Diphenylmethane (10 mL) was then added and the PhMe was removed in vacuo. The mixture was then heated to 250° C. for 2 h, cooled to r.t., the solids were removed by filtration, and washed with hexanes to give the title product as a tan solid. LRMS (M+H)+=307.9.

1. temperatureAfter cooling to r.t.
2. customthe EtOH and THF were removed in vacuo
3. washthe aqueous layer was washed with Et2O
4. extractionextracted with DCM two times
5. dry with materialThe organic layer was then dried over Na2SO4
6. customthe solvent was removed in vacuo

ORD record

ord-27ac4fb3b22f4035857c7954fb6173de

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927569B2