(4-Aminophenyl)(4-fluorophenyl)methanone → 1-(4-Aminophenyl)-1-(4-fluorophenyl)-2-propyn-1-ol

HRID 490016Notes

Reaction equation

HRID 490016 reaction equation
[C-:1]#[C-:2].[C-]#[C-].[Na+].[Na+].[NH2:7][C:8]1[CH:22]=[CH:21][C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1>C#C>[NH2:7][C:8]1[CH:22]=[CH:21][C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)([OH:13])[C:1]#[CH:2])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 577826(4-Aminophenyl)(4-fluorophenyl)methanone2×HCID 178420940HCID 178420940, compoundHCID 178463197HCID 178463197, compound

Product 1

HCID 876134721-(4-Aminophenyl)-1-(4-fluorophenyl)-2-propyn-1-ol

Reagents, catalysts & solvents 1

HCID 6326AcetyleneSolvent

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-1a5dcfb5600647a4b7ac5e22e5269b9e
Source dataset
uspto-grants-2009_05
Patent number
US07527754B2

Reaction notes

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