Toluene → [4-(3-Aminophenoxy)phenyl][4-(phenylethynyl)phenyl]methanone

HRID 1450011Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]1([C:15]#[C:16][C:17]2[CH:31]=[CH:30][C:20]([C:21]([C:23]3[CH:28]=[CH:27][C:26](F)=[CH:25][CH:24]=3)=[O:22])=[CH:19][CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>O.CC(N(C)C)=O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:26]1[CH:27]=[CH:28][C:23]([C:21]([C:20]2[CH:30]=[CH:31][C:17]([C:16]#[C:15][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:18][CH:19]=2)=[O:22])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 142 °C

Procedure

In a 500 mL flask equipped with nitrogen inlet, overhead stirring assembly, Dean-Stark trap, and reflux condenser were placed 3-aminophenol (18.5 g, 0.17 mol), 4-phenylethynyl-4'-fluorobenzophenone (43.2 g, 0.14 mol), potassium carbonate (22 g, 0.16 mol), toluene (30 mL), and DMAc (200 mL). The mixture was heated to 142° C. for 8 h, then cooled to room temperature. The reaction mixture was poured into water and the resulting light yellow powder was collected by filtration. Recrystallization from water/acetone (50/50) (v) and sodium dithionite (0.5 g) afforded 51.8 g (95% yield) of the desired product: m.p. 137°-139° C. IR (KBr); 3414 and 3342 cm-1 (NH2); 3040, 1596, and 1499 cm-1 (aromatic C--H); 2216 cm-1 (C≡C), and 1646 cm-1 (C=O): Mass Spec. m/e (relative intensity): M+, 389.4 (100); FW=389.44 g/mol.

Workup

customIn a 500 mL flask equipped with nitrogen inlet
temperatureDean-Stark trap, and reflux condenser
temperaturecooled to room temperature
filtrationthe resulting light yellow powder was collected by filtration
customRecrystallization from water/acetone (50/50) (v) and sodium dithionite (0.5 g)

Sources & evidence

ORD record: ord-0a61ee37e387468091689c785af83188
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05599993

Reaction notes

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