Allyl bromide → HCID 68964112, compound

HRID 2116070Notes

Reaction equation

HRID 2116070 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[C:10]1[C:11]([OH:16])=[CH:12][CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(Br)C=C.[CH2:27]([O:30]CC=C)[CH:28]=[CH2:29].C(C1C=CC=C(C2C(Cl)=CC(Cl)=CC=2Cl)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]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[C:10]1[C:11]2[O:16][CH:28]([CH2:27][OH:30])[CH2:29][C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

8

Reactant 6

HCID 7841Allyl bromideHCID 11194Diallyl etherHCID 11430Potassium Carbonate2×HCID 70297m-Chloroperbenzoic acidHCID 689640432',4',6'-Trichlorobiphenyl-2-olHCID 689681023-Allyl-2',4',6'-trichloro-1,1'-biphenyl-2-ol2×

Product 1

HCID 68964112HCID 68964112, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Procedure

Treatment of 2,4,6-trichlorobromobenzene (14.5 g, 55.69 mmol) with 2-methoxybenzeneboronic acid (12.69 g, 83.54 mol), dichlorobis(tri-o-tolylphosphine)-palladium(II) (0.656 g, 0.835 mmol), and potassium carbonate (19.21 g, 139.22 mmol) generally according to the procedure described for Intermediate 37 provided 9.8 g (61%) of 2′ 4′,6′-trichloro-1,1′-biphenyl-2-yl methyl ether. To a solution of 2′4′,6′-trichloro-1,1′-biphenyl-2-yl methyl ether (9.8 g, 34.08 mmol) in dichloromethane (100 mL) cooled to −78° C. was added boron tribromide (9.38 g, 1.0 M in dichloromethane) generally according to the procedure described for Intermediate 163 provided provided 9.2 g of a yellow solid. Treatment of 2′,4′,6′-trichloro-1,1′-biphenyl-2-ol (9.17 g, 33.52 mmol) with potassium carbonate (18.53 g, 134.1 mmol) and allyl bromide (4.46 g, 36.87 mol), followed by refluxing the resultant allyl ether in mesitylene generally according to the procedure described for Intermediate 8 provided 3-allyl-2′,4′,6′-trichloro-1,1′-biphenyl-2-ol. Treatment of 3-allyl-2′,4′,6′-trichloro-1,1′-biphenyl-2-ol. (10.35 g, 33.00 mmol) with 3-chloroperoxybenzoic acid (17.08 g, 99.00 mmol, 77%) followed by potassium carbonate (11.40 g, 82.51 mmol) generally according to the procedure described for Intermediate 9 afforded 10.4 g (95%) of (±)-[7-(2,4,6-trichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanol. Treatment of (±)-[7-(2,4,6-trichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanol (10.38 g, 31.49 mmol) with p-toluenesulfonyl chloride (7.20 g, 37.79 mol) generally according to the procedure described for Intermediate 10 gave 10.5 g (68%) of (±)-[7-(2,6-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate as a white solid. mp 178-180° C.

Sources & evidence

ORD record
ord-6807ff7388a2441397138f4ea90d3e85
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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