Trifluoroacetic acid → HCID 66920053, compound

HRID 1948678Notes

Reaction equation

HRID 1948678 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1.FC(F)(F)C(O)=O>O1CCCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[OH:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-oneHCID 178491912HCID 178491912, compound

Product 1

HCID 66920053HCID 66920053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.55 g (1.65 mmol ) of 7-bromo-1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalen-1-ol, obtained analogously to Example 1a) from 7-bromo-3,4-dihydro-2H-naphthalen-1-one and 4-methoxyphenyl-magnesium bromide, and 0.2 ml of trifluoroacetic acid in 20 ml of tetra-hydrofuran is warmed at 50° C. for 12 hours and subsequently evaporated to dryness. 10 ml of saturated sodium hydrogencarbonate are added to the residue, and the aqueous mixture is extracted twice with 10 ml of ethyl acetate each time. After the combined organic phases have been dried over sodium sulfate and the solvent has been stripped off, the crude product is purified by column chromatography on silica gel (petroleum ether ethyl acetate 9:1), giving 0.54 g of 7-bromo-1-(4-methoxyphenyl)-3,4-dihydronaphthalene; LC/MS: 338 (M+Na).

Sources & evidence

ORD record
ord-3f5aaf9c8adf4ccd8a2e181b1d270bf7
Source dataset
uspto-grants-2013_03
Patent number
US08399509B2

Reaction notes

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