Boron tribromide → 1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone

HRID 394057Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[CH:15]=[C:16]([O:19]C)[CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:29].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[CH:15]=[C:16]([OH:19])[CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 18 mg of 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone (INTERMEDIATE 2) in 1 mL of CH2Cl2 was added 0.1 mL of BBr3. The resulting mixture was stirred 30 min at 0° C., then warmed to room temperature and stirred at this temperature for 1 h. The mixture was concentrated and the resulting residue was purified preparative thin layer chromatography, eluting with 98:2 CH2Cl2-MeOH, to yield 1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone. Mass spectrum (ESI) 421.0 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.47 (d, J=8.0 Hz, 2H); 7.33 (t, J=8.0 Hz, 1H); 7.27 (m, 1H); 6.95, (m, 2H); 5.82 (s, 1H); 5.23 (s, 1H); 2.56-3.00 (m, 5H).

Workup

temperaturewarmed to room temperature
stirringstirred at this temperature for 1 h
concentrationThe mixture was concentrated
customthe resulting residue was purified preparative thin layer chromatography
washeluting with 98:2 CH2Cl2-MeOH

Sources & evidence

ORD record: ord-1e8adee929174475a71f54f0dcf61882
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809199B2

Reaction notes

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