(1,1'-Biphenyl)-2-ol → 1-(2-Fluoroethoxy)-2-phenylbenzene

HRID 1086010

Reaction equation

[H-].[Na+].[C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CS(O[CH2:21][CH2:22][F:23])(=O)=O>CN(C)C=O>[F:23][CH2:22][CH2:21][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of sodium hydride (60 % oil dispersion; 4.0 g) in N,N-dimethylformamide (100 ml), 2-phenylphenol (17.0 g) was added at a temperature of 0 to 5° C., and the resultant mixture was stirred at room temperature for 1 hour. 2-Fluoroethyl methanesulfonate (14.2 g) was added thereto. The resulting mixture was heated to 90° C., followed by stirring for 5 minutes. The reaction mixture was poured onto ice-water and extracted with ethyl acetate. The extract was washed with aqueous potassium carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent, toluene) to give 1-(2-fluoroethoxy)-2-phenylbenzene (Compound No. 20) (16.4 g). nD24.8 1.5796.

Workup

additionwas added at a temperature of 0 to 5° C.
additionThe reaction mixture was poured onto ice-water
extractionextracted with ethyl acetate
washThe extract was washed with aqueous potassium carbonate solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluting solvent, toluene)

Sources & evidence

ORD record: ord-00740c94dc8a4bf7910ad7562c902468
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05012004

Linked notes

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