4,4'-Difluorobenzophenone → (4-Aminophenyl)(4-fluorophenyl)methanone

HRID 490015Notes

Reaction equation

HRID 490015 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)([OH:11])C#C)=[CH:4][CH:3]=1.FC1C=CC(C(C2C=CC(F)=CC=2)=O)=CC=1>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 95824,4'-DifluorobenzophenoneHCID 876134721-(4-Aminophenyl)-1-(4-fluorophenyl)-2-propyn-1-ol

Product 1

HCID 577826(4-Aminophenyl)(4-fluorophenyl)methanone

Procedure

Referring now to FIG. 2, wherein one non-limiting approach to the 1-(4-aminophenyl)-1-(4-fluorophenyl)-2-propyn-1-ol is presented, 4,4′-difluorobenzophenone (7) is reacted with a secondary amine HNR′″R″″ to give the 4-amino-4′-fluorobenzophenone 8, where R′″ and R″″ may be the same as R36 and R37, respectively, as set forth and claimed herein. Acetylide anion, for example, sodium acetylide in acetylene saturated dimethylformamide, is added to the carbonyl of 4-amino-4′-fluorobenzophenone 8 to give, upon aqueous workup, 1-(4-aminophenyl)-1-(4-fluorophenyl)-2-propyn-1-ol 9.

Sources & evidence

ORD record
ord-bc6840b61a2f47df85eb97f708fd6de6
Source dataset
uspto-grants-2009_05
Patent number
US07527754B2

Reaction notes

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