Hydrochloric Acid → (5-Bromo-2-chlorophenyl)(4-ethyoxyphenyl)(methoxy)ethane

3.42 g of (5-bromo-2-chlorophenyl)(4-ethyoxyphenyl)methanol prepared according to example 1 and 10 ml of anhydrous THF were added into a 100-ml round-bottomed flask, and the resulting solution was cooled in ice-water bath and magnetically stirred. 0.40 g (60%) of solid NaH was added in portions, after which, the resulting mixture was stirred for another one hour, and then 1.70 g of dried MeI was added. The reaction mixture was stirred overnight at room temperature, poured carefully into 200 ml of ice water, and adjusted pH to 4-5 with concentrated hydrochloric acid. The resulting acidic mixture was extracted twice with 100 ml of dichloromethane. The combined extracts were washed with saturated NaCl solution, dried over anhydrous sodium sulfate, and evaporated to dryness on a rotary evaporator to afford a colorless oily product, which was (5-bromo-2-chlorophenyl)(4-ethyoxyphenyl)(methoxy)methane. ESI-MS, m/z=355.2 ([M(79Br)+1]), 357.2 ([M(81Br)+1]).

1. additionwere added into a 100-ml round-bottomed flask
2. stirringafter which, the resulting mixture was stirred for another one hour
3. stirringThe reaction mixture was stirred overnight at room temperature
4. extractionThe resulting acidic mixture was extracted twice with 100 ml of dichloromethane
5. washThe combined extracts were washed with saturated NaCl solution
6. dry with materialdried over anhydrous sodium sulfate
7. customevaporated to dryness on a rotary evaporator
8. customto afford a colorless oily product, which

ORD record

ord-b22a4f5db71b44d987b2e3c510bfbaf5

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062087B2