2-Fluoro-4-nitrotoluene → HCID 54324749, compound

HRID 1032809Notes

Reaction equation

HRID 1032809 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].FC1C=C([N+]([O-])=O)C=CC=1CBr.FC1C=C([N+]([O-])=O)C=CC=1CP(=O)(OCC)OCC.CC1(C)[O:48][CH:47]([CH2:49][O:50][C:51]2[CH:58]=[CH:57][C:54]([CH:55]=O)=[CH:53][CH:52]=2)[CH2:46][O:45]1>>[OH:48][CH:47]([CH2:46][OH:45])[CH2:49][O:50][C:51]1[CH:58]=[CH:57][C:54]([CH:55]=[CH:11][C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[F:1])=[CH:53][CH:52]=1

Participants

5

Reactant 4

HCID 740252-Fluoro-4-nitrotolueneHCID 20086821HCID 20086821, compoundHCID 218861321-(Bromomethyl)-2-fluoro-4-nitrobenzeneHCID 53879426Phosphonic acid, [(2-fluoro-4-nitrophenyl)methyl]-, diethyl ester

Product 1

HCID 54324749HCID 54324749, compound

Procedure

2-Fluoro-4-nitrotoluene (commercially available) was converted with the use of N-bromosuccimimide into the intermediate 2-fluoro-4-nitrobenzyl bromide, and subsequently into diethyl 2-fluoro-4-nitrobenzylphosphonate, in accordance with the specification of D. H. Wadsworth et al. in the Journal of Organic Chemistry, Vol. 30 (1965) p. 680-685. The title compound was prepared by the same procedure as described in Example 2. Making use of 23.6 g of 4-((2,2-dimethyl-1,3-dioxa-4-cyclopentyl)methyloxy)benzaldehyde and 29.1 g of diethyl 2-fluoro-4-nitrobenzyl phosphonate there were obtained in all 21 g of 4-(2,3-dihydroxypropyloxy)-2'-fluoro-4'nitrostilbene with a melting point of 110° C. and a clearing temperature of 129° C.

Sources & evidence

ORD record
ord-1a28a2179f8241b8a7b7a0a70ed700fa
Source dataset
uspto-grants-1990_09
Patent number
US04959448

Reaction notes

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