3-Bromopyridine → 1,1-Dimethoxy-2-hydroxy-2-(3-pyridyl)-3-(2,4-dichlorophenyl)-propane

HRID 1614183Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:15][CH3:16])[C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Li])[CH:18]=1.C([Li])CCC.BrC1C=NC=CC=1>C(OCC)C.O.C(O)(C)C>[CH3:16][O:15][CH:3]([O:2][CH3:1])[C:4]([OH:14])([C:19]1[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13]

Participants

Conditions

Temperature: 0 °C

Procedure

At -70° C., 88.9 g (0.337 mol) of 1,1-dimethoxy-3-(2,4-dichlorophenyl)propan-2-one in 100 ml of diethyl ether (Et2O) is dripped into a solution of 0.371 mol of 3-pyridyllithium in 1.1 liters of Et2O prepared from n-butyllithium and 3-bromopyridine. After half an hour at -70° C., the solution is slowly heated up to 0° C. Isopropanol and then water is added, and the reaction solution is extracted with 1N hydrochloric acid. The acidic aqueous phase is then neutralized with NaHCO3 and extracted with methylene chloride (CH2Cl2). After drying over Na2SO4, all the volatile constituents are removed in a rotary evaporator. A yellowish red oil is obtained. Yield: 56.1 g (48.7%).

Workup

customAt -70° C.
waitAfter half an hour at -70° C.
extractionthe reaction solution is extracted with 1N hydrochloric acid
extractionextracted with methylene chloride (CH2Cl2)
dry with materialAfter drying over Na2SO4, all the volatile constituents
customare removed in a rotary evaporator
customA yellowish red oil is obtained

Sources & evidence

ORD record: ord-4193d6ccfc91442397795e8525ea61e9
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196433

Reaction notes

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