(E)-3-(3-Bromo-1,4-naphthoquinon-2-yl)-2-methylpropenoic Acid → (E)-3-(3-chloro-1,4-naphthoquinon-2-yl)-2-propylpropenoic acid

HRID 1527706Notes

Reaction equation

HRID 1527706 reaction equation
[Cl:1][C:2]1[C:3](/[CH:16]=[C:17](\[CH2:21][CH2:22][CH3:23])/[C:18]([OH:20])=[O:19])=[C:4]([O:14]C)[C:5]2[C:10]([C:11]=1[O:12]C)=[CH:9][CH:8]=[CH:7][CH:6]=2.BrC1C(=O)C2C(=CC=CC=2)C(=O)C=1/C=C(\C)/C(O)=O>CC(C)=O>[Cl:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:14])[C:3]=1/[CH:16]=[C:17](\[CH2:21][CH2:22][CH3:23])/[C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 25235467(E)-3-(3-Bromo-1,4-naphthoquinon-2-yl)-2-methylpropenoic AcidHCID 68772573(E)-3-(3-chloro-1,4-dimethoxynaphthalen-2-yl)-2-propylpropenoic acid

Product 1

HCID 68775213(E)-3-(3-chloro-1,4-naphthoquinon-2-yl)-2-propylpropenoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 43b was prepared from 42b (0.053 g, 0.16 mmol) as described above for 39a to give 0.016 g (0.05 mmol, 33%) of the product as a yellow solid following flash chromatography (2:3 acetone:hexanes 0.5% AcOH) and recrystallization from Et2O/hexanes.

Workup

  1. customto give

Sources & evidence

ORD record
ord-2159dd73c7c944acbf4f3ecbaca2c43c
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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