1,3-Dibromopropane → 3-Bromopropyl 2-chloro-4-(2,2,2-trifluoroethoxy)phenyl ether

HRID 51079Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:4][C:3]=1[OH:14].[Br:15][CH2:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([F:12])([F:13])[F:11])[CH:5]=[CH:4][C:3]=1[O:14][CH2:18][CH2:17][CH2:16][Br:15]

Participants

Conditions

Temperature: 70 °C

Procedure

To a 110 ml DMF solution of 2-chloro-4-(2,2,2-trifluoroethoxy)phenol (5 g, 22.1 mmol) was added 1,3-dibromopropane (11.2 ml, 110 mmol) and cesium carbonate (9.34 g, 28.7 mmol). The resulting suspension was heated to 70° C. for 5 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel eluting with 10% dichloromethane/hexanes to give the title compound as a clear oil 4.37 g (57%).

Workup

customThe solvent was removed under reduced pressure
additionThe residue was diluted with AcOEt and 2N hydrochloric acid
customThe organic layer was separated
extractionthe aqueous layer was extracted twice with AcOEt
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customchromatographed on silica gel eluting with 10% dichloromethane/hexanes

Sources & evidence

ORD record: ord-ecdd914637784e7789d3e00ed980906a
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713508B2

Reaction notes

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