(E)-3-(3-Bromo-1,4-naphthoquinon-2-yl)-2-methylpropenoic Acid → (E)-3-(3-Fluoro-1,4-naphthoquinon-2-yl)-2-methylpropenoic Acid

HRID 1527707Notes

Reaction equation

HRID 1527707 reaction equation
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13]C)=[C:5]([F:15])[C:4]=1/[CH:16]=[C:17](\[CH3:21])/[C:18]([OH:20])=[O:19].BrC1C(=O)C2C(=CC=CC=2)C(=O)C=1/C=C(\C)/C(O)=O>CC(C)=O>[F:15][C:5]1[C:6](=[O:13])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3](=[O:2])[C:4]=1/[CH:16]=[C:17](\[CH3:21])/[C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 25235467(E)-3-(3-Bromo-1,4-naphthoquinon-2-yl)-2-methylpropenoic AcidHCID 46180317(E)-3-(1,4-dimethoxy-3-fluoronaphthalen-2-yl)-2-methylpropenoic acid

Product 1

HCID 25235425(E)-3-(3-Fluoro-1,4-naphthoquinon-2-yl)-2-methylpropenoic Acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 52 was prepared from 99d (0.097 g, 0.33 mmol) as described above for 39a to give 0.020 g (0.08 mmol, 23%) of the product as a yellow solid following flash chromatography (3:17 acetone:hexanes 0.5% AcOH) and recrystallization from Et2O/hexanes. (0.020 g E; 0.015 g E starting material; 0.023 g Z methyl ester)

Workup

  1. customto give

Sources & evidence

ORD record
ord-50d1770c510a45459c00b5b84e660936
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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