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

HRID 2116060노트

반응식

HRID 2116060 반응식
[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

참가 물질

8

반응물 6

HCID 7841Allyl bromideHCID 11194Diallyl etherHCID 11430Potassium Carbonate2회HCID 70297m-Chloroperbenzoic acidHCID 532185934'-Chloro-2'-methyl[1,1'-biphenyl]-2-olHCID 689641103-Allyl-4'-chloro-2'-methyl-1,1'-biphenyl-2-ol2회

생성물 1

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

시약·촉매·용매 1

HCID 7947Mesitylene용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-e3c1b597983440ce9d4f0b921961b64f
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07435837B2

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