Potassium Carbonate → 2',6'-Dichloro-2-methoxybiphenyl

HRID 2116048Notes

Reaction equation

HRID 2116048 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1Br.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:10][O:11][C:12]1[C:13]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 295681-Bromo-2,6-dichlorobenzeneHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 541514172',6'-Dichloro-2-methoxybiphenylYield 77.2%

Reagents, catalysts & solvents 1

HCID 178424406HCID 178424406, compoundCatalyst

Procedure

Treatment of 2,6-dichlorobromobenzene (25.0 g, 0.110 mol) with 2-methoxybenzeneboronic acid (25.22 g, 0.166 mol), dichlorobis(tri-o-tolylphosphine)-palladium(II) (2.33 g, 2.96 mmol), and potassium carbonate (34.15 g, 0.247 mmol) generally according to the procedure described for Intermediate 37 provided 21.5 g (77%) of 2′,6′-dichloro-1,1′-biphenyl-2-yl methyl ether. Treatment of 2′,6′-dichloro-1,1′-biphenyl-2-yl methyl ether (19.0 g, 75.06 mmol) with boron tribromide (18.78 g, 1.0 M in dichloromethane) generally according to the procedure described for Intermediate 163 provided 17.89 g (99%) of 2′,6′-dichloro-111′-biphenyl-2-ol as a light yellow solid. mp 100-103° C.; Anal. calcd. for C12H8Cl2O: C, 60.28H, 3.37. Found: C, 60.29; H, 3.13.

Sources & evidence

ORD record
ord-4bbb160a5762433aadff35a82617e7c8
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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