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

HRID 873040Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][C:9]=1[C:10]#[N:11].[F:18][C:19]([F:28])([F:27])[C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1>CN(C=O)C>[CH:16]([C:13]1[CH:14]=[CH:15][C:8]([O:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([C:19]([F:18])([F:27])[F:28])[CH:21]=2)=[C:9]([CH:12]=1)[C:10]#[N:11])=[O:17]

Participants

Conditions

Temperature: 60 °C

Procedure

Potassium carbonate (1.85 g, 13.41 mmol) was added to a solution of 2-fluoro-5-formylbenzonitrile (2.0 g, 13.41 mmol) and 3-trifluoromethyl-phenol (1.63 mL, 13.41 mmol) in DMF (10 mL). The reaction mixture was stirred at 60° C. for 2 h with microwave radiation. The resultant mixture was filtrated, and then concentrated. Purification via Flash Chromatography (FC) afforded the title compound as a white solid (3 g, 73% yield).

Workup

filtrationThe resultant mixture was filtrated
concentrationconcentrated
customPurification via Flash Chromatography (FC)

Sources & evidence

ORD record: ord-36f70daa05e44e068c63c3bad42d47d3
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975400B2

Reaction notes

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