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

HRID 2116060Notes

Reaction equation

HRID 2116060 reaction equation
[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

Participants

8

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Procedure

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.

Sources & evidence

ORD record
ord-e3c1b597983440ce9d4f0b921961b64f
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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