Cyclohexanone → 4-[(4-Bromo-2-chlorophenyl)(cyclohexylidene)methyl]phenol

TiCl4 (2.01 mL, 18.2 mmol) was added dropwise to a suspension of zinc powder (2.41 g, 36.9 mmol) in anhydrous THF (60 mL) at RT. After refluxing for 1 h, a mixture of 71 (1.42 g, 4.56 mmol) and cyclohexanone (1.34 g, 13.7 mmol) dissolved in THF (20 mL) was added dropwise. Refluxing was continued for 30 min. The reaction mixture was cooled to RT and filtered through Celite. Water (250 mL) was added and the mixture was extracted with Et2O (3×100 mL). The combined ethereal extracts were washed with water (200 mL), brine (200 mL), and dried over MgSO4. Concentration followed by flash chromatography (20:1 to 5:1 hexanes:EtOAc) afforded 1.61 g (93%) of compound 72 as a light green oil. 1H NMR (400 MHz, CDCl3): δ 1.59 (m, 6H), 1.97 (m, 2H), 2.28 (m, 2H), 4.93 (br s, 1H), 6.72 (d, J=8.6 Hz, 2H), 7.04 (m, 3H), 7.32 (dd, J=8.2 Hz, 2.0 Hz, 1H), 7.51 (d, J=2.0 Hz, 1H).

1. temperatureAfter refluxing for 1 h
2. additionwas added dropwise
3. temperatureRefluxing
4. filtrationfiltered through Celite
5. additionWater (250 mL) was added
6. extractionthe mixture was extracted with Et2O (3×100 mL)
7. washThe combined ethereal extracts were washed with water (200 mL), brine (200 mL)
8. dry with materialdried over MgSO4
9. concentrationConcentration

ORD record

ord-b7b58c639c5d410d8337f8cac48c4ef9

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560589B2