Hydrochloric Acid → HCID 86622343, compound

Temperature

-78 °C

Step AJ (2): To a solution of 1-bromo-2-(dimethoxymethyl)-4-(trifluoromethyl)benzene (1060 mg, 3.544 mmol) in THF (10 mL) at −78° C. was added 1.6N solution of n-butyl lithium in hexanes (4.43 mL, 7.088 mmol). The resulting mixture was stirred at −78° C. for 15 min. 5-Bromopent-1-ene (0.42 mL, 3.544 mmol) was added by drops. The reaction mixture was warmed to rt and stirred overnight. Aqueous hydrochloric acid solution (1N) was added and the reaction mixture was stirred at rt for 3 h. The reaction was extracted with DCM. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography to give 2-(pent-4-enyl)-5-(trifluoromethyl)benzaldehyde (858.0 mg, 100%) as a brown oil. LC-MS (M+H)+=243.09. 1H NMR (CDCl3, 500 MHz) δ 10.30 (s, 1H) 8.22-7.35 (m, 3H) 7.06 (m, 1H) 5.83 (m, 1H) 5.10-5.00 (m, 2H) 3.84 (s, 3H) 2.16 (m, 2H) 1.75 (m, 2H) 1.60 (m, 2H).

1. temperatureThe reaction mixture was warmed to rt
2. stirringstirred overnight
3. stirringthe reaction mixture was stirred at rt for 3 h
4. extractionThe reaction was extracted with DCM
5. dry with materialThe combined organic phases were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuum
8. customThe residue was purified by silica gel chromatography

ORD record

ord-b6c27a67cbd14c389718437c0fe652d3

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772221B2