Allyl bromide → (+/-)-[7-(4-Chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanol

HRID 2116060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2116060
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([OH:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:4]([CH3:15])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(Br)C=C.[CH2:26]([O:29]CC=C)[CH:27]=[CH2:28].C(C1C=CC=C(C2C=CC(Cl)=CC=2C)C=1O)C=C.ClC1C=C(C=CC=1)C(OO)=O>C1(C)C=C(C)C=C(C)C=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[O:14][CH:27]([CH2:26][OH:29])[CH2:28][C:10]=3[CH:11]=[CH:12][CH:13]=2)=[C:4]([CH3:15])[CH:3]=1

Komponenten

8

Edukt 6

HCID 7841Allyl bromideHCID 11194Diallyl etherHCID 11430Potassium Carbonate2×HCID 70297m-Chloroperbenzoic acidHCID 532185934'-Chloro-2'-methyl[1,1'-biphenyl]-2-olHCID 689641103-Allyl-4'-chloro-2'-methyl-1,1'-biphenyl-2-ol2×

Produkt 1

HCID 68964315(+/-)-[7-(4-Chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanolAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7947MesityleneLösungsmittel

Versuchsvorschrift

Treatment of 4′-chloro-2′-methyl-1,1′-biphenyl-2-ol (4.54 g, 20.78 mmol) with potassium carbonate (11.47 g, 83.04 mmol) and allyl bromide (3.01 g, 24.91 mol), followed by refluxing the resultant allyl ether in mesitylene generally according to the procedure described for Intermediate 8 provided 3-allyl-4′-chloro-2′-methyl-1,1′-biphenyl-2-ol. Treatment of 3-allyl-4′-chloro-2′-methyl-1,1′-biphenyl-2-ol (4.5 g, 17.39 mmol) with 3-chloroperoxybenzoic acid (12.0 g, 69.57 mmol, 77%) followed by potassium carbonate (6.0 g, 43.48 mmol) generally according to the procedure described for Intermediate 9 afforded 2.9 g (61%) of (±)-[7-(4-chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanol as a colorless oil. Anal. calcd. for C16H15ClO2: C, 69.95; H, 5.5. Found: C, 69.23; H, 5.42.

Quellen und Nachweise

ORD-Eintrag
ord-e3c1b597983440ce9d4f0b921961b64f
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435837B2

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