Water → 1-[4-(9H-Carbazol-9-yl)phenyl]ethanone

HRID 37757

Reaction equation

[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:14][C:15]([C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=1)=[O:16].C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH:10]1[C:11]2[N:12]([C:20]3[CH:21]=[CH:22][C:17]([C:15](=[O:16])[CH3:14])=[CH:18][CH:19]=3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 135 °C

Procedure

To carbazole (5.02 g) in DMSO (50 mL) is added 4-fluoroacetophenone (3.45 g) and K2CO3 (10.4 g), and the mixture is stirred at 135° C. overnight. The mixture is poured into water to afford a precipitate, which is isolated by filtration and washed with water. The crude product thus obtained is further purified by recrystallization from TBME (tert-butyl methyl ether), giving the product as a light brown solid. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 2.71 (s, 3H), 7.32 (ddd, 2H), 7.41-7.50 (m, 4H), 7.72 (d, 2H), 8.15 (d, 2H), 8.21 (d, 2H).

Workup

customto afford a precipitate
customwhich is isolated by filtration
washwashed with water
customThe crude product thus obtained
customis further purified by recrystallization from TBME (tert-butyl methyl ether)

Sources & evidence

ORD record: ord-0d65275dc5704080bbbbe2b39cde242f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524425B2

Linked notes

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