Potassium Carbonate → 1-Benzyl-4-chloro-2-methoxybenzene

HRID 272744Notes

Reaction equation

HRID 272744 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[O:10][CH3:11].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:2]([C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[O:10][CH3:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 223274741-(Bromomethyl)-4-chloro-2-methoxybenzene

Product 1

HCID 692167101-Benzyl-4-chloro-2-methoxybenzeneYield 18.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-Bromomethyl-4-chloro-2-methoxy-benzene (50 mg, 0.21 mmol), phenyl boronic acid (28 mg, 0.23 mmol), Pd(PPh3)4 (24 mg, 0.021 mmol) and K2CO3 (87 mg, 0.63 mmol) were combined in dioxane, purged with N2, and heated to reflux for 16 hours. The mixture was then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel eluting with 4:1 hexanes/ethyl acetate to provide 9 mg (18%) of the title compound. MS (ESI) m/e 233 (M+H)+.

Workup

  1. custompurged with N2
  2. temperatureheated
  3. temperatureto reflux for 16 hours
  4. customThe mixture was then partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash column chromatography on silica gel eluting with 4:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-cd67fa8b66294287b5b57e87a2dce8c8
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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