Potassium Carbonate → 4'-Chloro-2'-methyl-1,1'-biphenyl-2-yl methyl ether

HRID 2116058Notes

Reaction equation

HRID 2116058 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH3:9].[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:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=2[CH3:9])=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 844762-Bromo-5-chlorotolueneHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 689666184'-Chloro-2'-methyl-1,1'-biphenyl-2-yl methyl etherYield 89.2%

Reagents, catalysts & solvents 1

HCID 178424406HCID 178424406, compoundCatalyst

Procedure

Treatment of 2-bromo-5-chlorotoluene (5.0 g, 24.33 mmol) with 2-methoxybenzeneboronic acid (4.8 g, 31.63 mmol), dichlorobis(tri-o-tolylphosphine)-palladium(II) (0.478 g, 0.608 mmol), and potassium carbonate (8.41 g, 60.83 mmol) generally according to the procedure described for Intermediate 37 provided 5.05 g (89%) of 4′-chloro-2′-methyl-1,1′-biphenyl-2-yl methyl ether. Treatment of 4′-chloro-2′-methyl-1,1′-biphenyl-2-yl methyl ether (5.05 g, 21.48 mmol) with boron tribromide (5.37 g, 1.0 M in dichloromethane) generally according to the procedure described for Intermediate 163 provided 4.58 g (97%) of 4′-chloro-2′-methyl-1,1′-biphenyl-2-ol as a yellow oil. Anal. calcd. for C13H11ClO: C, 71.4; H, 5.07. Found: C, 71.03; H, 4.84.

Sources & evidence

ORD record
ord-0ac4e4d4c2ff4066bb65aed11e95d555
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…