Boron tribromide → 4-{[2-Hydroxy-4,4-dimethyl-5-methoxy-2-trifluoromethyl-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-phthalide

HRID 1443196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443196
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([CH3:20])([CH3:19])[CH2:10][C:11]([OH:18])([C:14]([F:17])([F:16])[F:15])[CH:12]=O.[NH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[CH2:24][O:25][C:26]2=[O:27].B(Br)(Br)Br>>[OH:18][C:11]1([C:14]([F:15])([F:17])[F:16])[CH2:10][C:9]([CH3:19])([CH3:20])[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH:12]1[NH:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[CH2:24][O:25][C:26]2=[O:27]

Komponenten

4

Edukt 3

HCID 25134Boron tribromideHCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-oneHCID 179890984-(2-Methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

Produkt 1

HCID 686800504-{[2-Hydroxy-4,4-dimethyl-5-methoxy-2-trifluoromethyl-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-phthalideAusbeute 19 %

Versuchsvorschrift

Analogously to Example 10, the corresponding imine is produced starting from 600 mg of 4-(2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 308 mg of 4-amino-phthalide (Bull. Soc. Sci. Bretagne 26, 1951, Special Edition 5, p. 7, 96). As in Example 2, 650 mg of the imine is reacted by reaction with 7.7 ml of BBr3 (1 M in dichloromethane), and 165 mg of the title compound is obtained.

Quellen und Nachweise

ORD-Eintrag
ord-17b88a861a8e4f0f8853434cefe555a5
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659297B2

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