4,4'-Difluorobenzophenone → HCID 14423937, compound

HRID 1199175Notes

Reaction equation

[CH2:1]([C:3]1[N:7]([CH3:8])[N:6]=[N:5][N:4]=1)[CH3:2].C([Li])CCC.[F:14][C:15]1[CH:29]=[CH:28][C:18]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[O:20])=[CH:17][CH:16]=1>O1CCCC1.CCCCCC>[F:14][C:15]1[CH:29]=[CH:28][C:18]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)([OH:20])[CH:1]([C:3]2[N:7]([CH3:8])[N:6]=[N:5][N:4]=2)[CH3:2])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 5-ethyl-1-methyl-1H-tetrazole (5.6 g, 0.05 mole) [prepared in Step A] in 60 mL of dry tetrahydrofuran was added 2.5M n-butyllithium (20 mL, 0.05 mole) in hexane over 5 minutes at -78° C. (bath temperature) under an inert atmosphere. The mixture was stirred for 30 minutes and a solution of 4,4'-difluorobenzophenone (10.8 g, 0.5 mole) in 25 mL of dry tetrahydrofuran was added over 5 minutes. This mixture was stirred for an additional 2 hours while the bath temperature was slowly warmed to -20° C. The reaction was quenched with 1N HCl and extracted with ethyl acetate (3×50 mL) and chloroform (3×50 mL). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to give a white solid. The solid was purified by crystallization from ethanol-hexane to give 10.8 g (65%) of the title compound; m.p.=160°-161° C.

Workup

stirringThis mixture was stirred for an additional 2 hours while the bath temperature
customThe reaction was quenched with 1N HCl
extractionextracted with ethyl acetate (3×50 mL) and chloroform (3×50 mL)
dry with materialThe combined organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customto give a white solid
customThe solid was purified by crystallization from ethanol-hexane

Sources & evidence

ORD record: ord-0acbce2e6b144f149873662d54c6fbcd
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04898950

Reaction notes

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