Diethyl Ether → 1-Chloro-3-ethenyl-2-[(propan-2-yl)oxy]benzene

Temperature

60 °C

2-chloro-6-vinylphenol (1.55 g, 10 mmol) and 2-iodopropance (1.5 ml, 15 mmol, 1.5 equiv) were dissolved in DMF, followed by adding K2CO3 (3.9 g, 30 mmol) into DMF solution, then heated at 60° C. overnight. etherification was monitored by TLC and HPLC until completed. The mixture was diluted with Et2O (250 mL), and washed with water (2×200 mL). The aqueous layer was extracted twice with Et2O (150 mL), and the combined organic layers were washed with brine, and dried over MgSO4. The product was purified by flash column (Hexanes:Et2O=6:1) to offer 1.69 g of product 4a (Yield: 82%, purity: 98%). 1HNMR (CDCl3: δ=7.26 ppm): 7.42 (dd, 1H, J=1.56, 7.82 Hz), 7.29 (dd, 1H, J=1.56, 7.83 Hz), 7.02 (m, 2H), 5.73 (d, 1H, J=17.60 Hz), 5.56 (d, 1H, J=11.34 Hz), 4.43 (m, 1H), 1.32 (d, 6H, J=6.26 Hz). (M+H+): m/z calculated: 197.1. found: 197.1.

1. washwashed with water (2×200 mL)
2. extractionThe aqueous layer was extracted twice with Et2O (150 mL)
3. washthe combined organic layers were washed with brine
4. dry with materialdried over MgSO4
5. customThe product was purified by flash column (Hexanes:Et2O=6:1)

ORD record

ord-c77291ea5cbb4f378298dc82577f6227

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288576B2