Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 66602974, compound

Temperature

65 °C

Into a flame-dried 250 mL round-bottomed flask were added 5-bromo-2-methoxy-phenol (10.01 g, 49.3 mmol), 2-chloroethyl-p-toluenesulfonate (25.32 g, 107.9 mmol), CsCO3 (20.43 g, 62.7 mmol), Triton X-405 (0.57 g, 1 mmol), and THF (55 mL). The slurry was heated at 65° C. for 7 h, then cooled to room temperature. The reaction solution was cooled to 0° C., and a solution of potassium tert-butoxide (18.11 g, 1.48 mol) in 100 mL THF was added dropwise over 30 min. The reaction mixture was allowed to warm to room temperature and stirred an additional 2.5 h. The reaction was quenched by addition of a saturated aqeuous NH4Cl solution, and extracted 3× with EtOAc. The combined organic phase was treated with brine, dried over MgSO4, filtered, concentrated, and then co-evaporated 3× with toluene. The intermediate 4-bromo-1-methoxy-2-vinyloxy-benzene was obtained as an orange-tinted oil (12.2 g). 1H NMR (DMSO-d6) 7.26 (dd, J=8.8, 2.4, 1H), 7.20 (d, J=2.4 Hz, 1H), 6.77 (dd, J=13.6, 6.0, 1H), 4.63 (d, J=13.6, 1H), 4.42 (d, J=6.0, 1H), 3.76 (s, 3H).

1. temperaturecooled to room temperature
2. temperatureThe reaction solution was cooled to 0° C.
3. temperatureto warm to room temperature
4. customThe reaction was quenched by addition of a saturated aqeuous NH4Cl solution
5. extractionextracted 3× with EtOAc
6. additionThe combined organic phase was treated with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-f076c0db21034a8289417e246ed39a66

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927546B2