4,4'-Difluorobenzophenone → HCID 15133036, compound

HRID 1086066Notes

Reaction equation

C([N-]C(C)C)(C)C.[Li+].[CH:9]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[F:21][C:22]1[CH:36]=[CH:35][C:25]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1>O1CCCC1>[CH:9]1([CH:15]([C:26]([C:25]2[CH:35]=[CH:36][C:22]([F:21])=[CH:23][CH:24]=2)([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[OH:27])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: -70 °C

Procedure

Lithium diisopropylamide (56 mL of 1.8M, 100 mmol) was added to a solution of ethyl cyclohexylacetate (16.0 g, 100 mmol) in 50 mL tetrahydrofuran at -40° C. and the solution stirred for 0.5 hour. After further cooling to -70° C., 4,4'-difluorobenzophenone (10.9 g, 50 mmol) was added and the solution stirred for 1 hour at -70° C. and then allowed to warm to -10° C. during the next 2 hrs. The reaction was quenched with 2N hydrochloric acid and extracted with diethyl ether. The extracts were dried with magnesium sulfate and concentrated in vacuo. The residue was crystallized from hexane to give 158 g of the title compound; m.p. =118°-119° C.

Workup

stirringthe solution stirred for 1 hour at -70° C.
temperatureto warm to -10° C. during the next 2 hrs
customThe reaction was quenched with 2N hydrochloric acid
extractionextracted with diethyl ether
dry with materialThe extracts were dried with magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was crystallized from hexane

Sources & evidence

ORD record: ord-2b288c349c0c4762a78acacfe52bfd21
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05011947

Reaction notes

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