5-Benzyloxy-2-bromotoluene → HCID 70856270, compound

HRID 1474664Notes

Reaction equation

HRID 1474664 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](Br)=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[C:18]([O:22][C:23](=[O:26])[CH2:24][Zn+])([CH3:21])([CH3:20])[CH3:19].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1COCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:24][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:26])=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 27566395-Benzyloxy-2-bromotolueneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 178451183HCID 178451183, compound

Product 1

HCID 70856270HCID 70856270, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-benzyloxy-2-bromotoluene (1 g, 3.61 mmol) in THF (10 ml) was added 2-tert-butoxy-2-oxoethylzinc chloride (18.04 ml, 9.02 mmol). Nitrogen gas bubbled through the mixture for 10 min. then Pd2(dba)3 (0.165 g, 0.180 mmol) and X-PHOS (0.172 g, 0.361 mmol) were added and the resulting mixture heated at 60° C. for 50 min. The mixture was cooled, diluted with ethyl acetate (20 mL), washed with aqueous ammonium chloride (saturated, 1×15 mL), dried over MgSO4, filtered and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (Biotage 50M), using a gradient eluant of EtOAc/Hexane (0-20%) to afford the title compound. LC/MS (m/z): 335 (M+Na)+.

Workup

  1. customNitrogen gas bubbled through the mixture for 10 min.
  2. temperatureThe mixture was cooled
  3. washwashed with aqueous ammonium chloride (saturated, 1×15 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (Biotage 50M)

Sources & evidence

ORD record
ord-08ba8d3c801b417fab491b8ce48d66f6
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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