Potassium Carbonate → Benzonitrile, 2-[4-chloro-3-(trifluoromethyl)phenoxy]-5-formyl-

HRID 536149Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=1[C:20]([F:23])([F:22])[F:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:3]=2[C:4]#[N:5])=[CH:15][C:14]=1[C:20]([F:21])([F:22])[F:23]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-fluoro-5-formylbenzonitrile (5.0 g, 33.5 mmol), 4-chloro-3-(trifluoromethyl)phenol (6.59 g, 33.5 mmol) and potassium carbonate (13.9 g, 101 mmol) in N,N-dimethyl formamide (DMF) (10 mL) was stirred at 60° C. overnight and filtered. Purification via Biotage-C18 system afforded the title product (6 g) as a pale solid. LC-MS (ESI): m/z 326 [M+H]+; 3.51 min (ret time).

Workup

filtrationfiltered
customPurification via Biotage-C18 system

Sources & evidence

ORD record: ord-58891d9aec9e4250a1662eb66466f57f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859573B2

Reaction notes

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