Fluorine → Diethyl fluoro(nitro)propanedioate

HRID 380068Notes

Reaction equation

[N+:1]([CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])([O-:3])=[O:2].[F:15]F>>[CH2:8]([O:7][C:5](=[O:6])[C:4]([F:15])([N+:1]([O-:3])=[O:2])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:9]

Participants

Reactant 2

HCID 24524Fluorine

HCID 97657Diethyl nitromalonate2×

Product 1

HCID 284709Diethyl fluoro(nitro)propanedioateYield 76%

Procedure

An experiment was carried out as described in Example 2 using diethyl nitromalonate instead of diethyl malonate. Thus, 4.1 gm. (20 mmol.) diethylnitromalonate was treated with fluorine to give diethylfluoronitromalonate {δH 1.40 (6H, t, JHH 7.11, CH3), 4.47 (4H, q, JHH 7.12, CH2); δF 127.3 δC 13.7 (s, CH3), 65.2 (s, CH2), 106.3 (d, 1JCF 261.7, CF), 157.9 (d. 2JCF 25.2, CO).} in 76% yield. The conversion was 97%.

Sources & evidence

ORD record: ord-50c760087b1a49e9ab784be95afff4c9
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300511B1

Reaction notes

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