Diisopropylethylamine → Diethyl 5-(4-fluorophenyl)-2-furanphosphonate

HRID 895991

Reaction equation

I[C:2]1[O:6][C:5]([P:7]([O:12][CH2:13][CH3:14])(=[O:11])[O:8][CH2:9][CH3:10])=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.CC#N.CC#N.Cl[Pd]Cl>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[O:6][C:5]([P:7]([O:12][CH2:13][CH3:14])(=[O:11])[O:8][CH2:9][CH3:10])=[CH:4][CH:3]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of diethyl 5-iodo-2-furanphosphonate (1 mmol), 4-fluorophenylboronic acid (2 mmol), diisopropylethylamine (DIEA) (4 mmol) and bis(acetonitrile)dichloropalladium(II) (0.05 mmol) in 6 mL DMF was heated at 75° C. for 16 h. Extraction and chromatography provided diethyl 5-(4-fluorophenyl)-2-furanphosphonate as an oil.

Workup

extractionExtraction and chromatography

Sources & evidence

ORD record: ord-cea20ef400b64a899f717c7737dd3f75
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919322B2

Linked notes

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