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

HRID 902298

Reaction equation

HRID 902298 reaction equation
Br[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[Cl: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+]>O1CCOCC1.O.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.Cl[Pd]Cl>[CH3:10][O:11][C:12]1[C:13]([C:2]2[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=2[Cl:9])=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 3

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

Product 1

HCID 541514172',6'-Dichloro-2-methoxybiphenylYield 49.2%

Reagents, catalysts & solvents 3

HCID 10876480Bis(tri-o-tolylphosphine)palladium(II) DichlorideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-bromo-2,6-dichlorobenzene (5.0 g, 0.022 mol), 2-methoxyphenylboronic acid (5.045 g, 0.033 mol) and potassium carbonate (7.65 g, 0.055 mol) in dioxane (130 mL) and water (13 mL) was purged with nitrogen for 20 minutes. Trans-dichlorobis(tri-o-tolylphosphine)palladium (II) (0.87 g, 0.0011 mol) was added and the reaction mixture heated to 100° C. for 36 hours. The cooled reaction mixture was then filtered through celite washing the filter cake with ethyl acetate. The combined organic filtrates were diluted to 500 mL by the addition of ethyl acetate, then washed with 2.0 M aqueous sodium hydroxide (2×350 mL), water (350 mL) and saturated brine (350 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford a yellow oil. Purification by flash chromatography using a solvent gradient of 0.5 to 2% ethyl acetate in hexane gave 2.74 g (49%) of 2′,6′-dichloro-1,1′-biphenyl-2-yl methyl ether as a white solid. MS (EI) m/z 252 (M+).

Workup

  1. customwas purged with nitrogen for 20 minutes
  2. customThe cooled reaction mixture
  3. filtrationwas then filtered through celite
  4. washwashing the filter cake with ethyl acetate
  5. additionThe combined organic filtrates were diluted to 500 mL by the addition of ethyl acetate
  6. washwashed with 2.0 M aqueous sodium hydroxide (2×350 mL), water (350 mL) and saturated brine (350 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford a yellow oil
  11. customPurification by flash chromatography

Sources & evidence

ORD record
ord-33c104223afd44648e4e55f7dffb268c
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Linked notes

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