(E)-3-(3-Bromo-1,4-naphthoquinon-2-yl)-2-methylpropenoic Acid → 3-(3-Chloro-1,4-dihydronaphthalen-2-yl)-2-methylacrylic acid

HRID 1527705Notes

Reaction equation

HRID 1527705 reaction equation
[Cl:1][C:2]1[C:3](/[CH:16]=[C:17](\[CH3:21])/[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](\[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 46180319(E)-3-(3-chloro-1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoic acid

Product 1

HCID 252354263-(3-Chloro-1,4-dihydronaphthalen-2-yl)-2-methylacrylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 43a was prepared from 42a (0.872 g, 2.84 mmol) as described above for 39a to give 0.121 g (0.437 mmol, 16%) of the product as a yellow solid following flash chromatography (2:3 acetone:hexanes 0.5% AcOH) and recrystallization from Et2O/hexanes. (0.121 g E; 0.115 g Z methyl ester)

Workup

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Sources & evidence

ORD record
ord-7d4815dec19844c08c0afe7b8f56bc9c
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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