Ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate → Ethyl 2-oxo-2-(10-(trifluoromethylsulfonyloxy)phenanthren-9-yl)acetate

HRID 926193Notes

Reaction equation

HRID 926193 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[C:7]([C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:6]([CH3:27])=[CH:5]2.O[CH:29]([C:35]1C2C(C3C=CC=CC=3C=1O)=CC=CC=2)[C:30](OCC)=O>>[O:26]=[C:20]([C:7]1[C:6]2[C:5]([C:4]3[CH:3]=[CH:2][CH:11]=[CH:10][C:9]=3[C:8]=1[O:12][S:13]([C:16]([F:17])([F:19])[F:18])(=[O:15])=[O:14])=[CH:35][CH:29]=[CH:30][CH:27]=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

3

Reactant 2

HCID 89676645Ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetateHCID 89676749Ethyl 2-hydroxy-2-(10-hydroxyphenanthren-9-yl)acetate

Product 1

HCID 89676702Ethyl 2-oxo-2-(10-(trifluoromethylsulfonyloxy)phenanthren-9-yl)acetate

Procedure

Prepared by the similar method to make ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate in Example 20, using ethyl 2-hydroxy-2-(10-hydroxyphenanthren-9-yl)acetate instead of ethyl 2-(6-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate. 1H-NMR: 400 MHz, (CDCl3) δ: 8.77-8.74 (m, 2H), 8.25 (d, J=4.0 Hz, 1H), 7.87-7.84 (m, 2H), 7.81-7.77 (m, 2H), 7.70-7.67 (m, 2H), 4.44-4.38 (m, 2H), 1.37 (t, J=7.2 Hz, 3H). 17F-NMR: 400 MHz, (CDCl3) δ: −73.18 (s).

Workup

  1. customPrepared by the similar method

Sources & evidence

ORD record
ord-65ea945e4fc74f97ad29998415855147
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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