3-(Trifluoromethyl)benzoyl chloride → 8-nitro-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-one

HRID 876520Notes

Reaction equation

[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].[F:14][C:15]([F:26])([F:25])[C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=O.C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1>[N+:8]([C:7]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:2]=1[O:1][C:19]([C:18]1[CH:22]=[CH:23][CH:24]=[C:16]([C:15]([F:14])([F:25])[F:26])[CH:17]=1)=[CH:12][C:11]2=[O:13])([O-:10])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

1-(2-Hydroxy-3-nitrophenyl)ethanone 1 (1.2 g, 6.61 mmol) was taken up in 20 mL of pyridine along with 3-trifluoromethylbenzoyl chloride 48 (1.2 mL, 7.9 mmol) and DBU (2.9 mL, 14.5 mmol). The reaction mixture was stirred at 80° C. for 18 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was diluted with EtOAc and washed with dilute 1 N HCl. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (1:1 pentane/EtOAc) afforded 300 mg of 2. MS (ESI) calcd for C16H8F3NO4: 335.04. found: 336 [M+H].

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
additionThe resulting residue was diluted with EtOAc
washwashed
additionwith dilute 1 N HCl
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated under reduced pressure
customPurification by chromatography (1:1 pentane/EtOAc)

Sources & evidence

ORD record: ord-928015df78a5405ab542fbf84c48df05
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987258B2

Reaction notes

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