3-(Trifluoromethyl)phenol → Benzonitrile, 5-formyl-2-[3-(trifluoromethyl)phenoxy]-

HRID 474632Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-(trifluoromethyl)phenol (1.435 g, 8.85 mmol) and 2-fluoro-5-formylbenzonitrile (1.2 g, 8.05 mmol) in DMF (25 mL) was added K2CO3 (3.34 g, 24.14 mmol) under argon. The mixture was heated at 90° C. for 0.5 h. After removing the solvent, the residue was diluted with water, extracted with DCM. The organic phase was dried over sodium sulfate, filtered, and concentrated. Recrystallization in EA then afforded the title compound (2.5 g, 8.58 mmol, 107% yield). LCMS: rt=3.34 min, [M+H+]=292

Workup

customAfter removing the solvent
additionthe residue was diluted with water
extractionextracted with DCM
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customRecrystallization in EA

Sources & evidence

ORD record: ord-60f5f496286b42a9847e8950f9e67f6e
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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