Hydrochloric Acid → 2-[4-({3-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy}methyl)phenyl]ethanol

HRID 2104601Notes

Reaction equation

HRID 2104601 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:19]([F:22])([F:21])[F:20].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][OH:33])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][OH:33])=[CH:27][CH:26]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:19]([F:22])([F:20])[F:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 223370184-(Bromomethyl)benzeneethanolHCID 665862653-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenol

Product 1

HCID 669142542-[4-({3-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy}methyl)phenyl]ethanolYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenol (0.086 g, 0.28 mmol) and 2-(4-bromomethlyphenyl)ethanol (0.061 g, 0.28 mmol) in CH2Cl2 (5 mL) is added Cs2CO3 (0.365 g, 1.12 mmol). After 1.5 h, additional alkylating agent (0.015 g) is added and the reaction is stirred overnight. The reaction is neutralized with 2N aq HCl, extracted with ethyl acetate and dried (MgSO4). Chromatography eluting with 5:95 ethyl acetate:hexane afforded the title compound (0.092 g, 75%).

Workup

  1. additionadditional alkylating agent (0.015 g) is added
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. washChromatography eluting with 5:95 ethyl acetate

Sources & evidence

ORD record
ord-e0e0b693af6f46db9745ffadb48f7694
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

Loading…