2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → Tert-butyl 2-(4-benzyloxy-2-methoxyphenyl)acetate

HRID 1474683Notes

Reaction equation

HRID 1474683 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[C:11]([O:16][CH3:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[C:19]([O:23][C:24](=[O:27])[CH2:25][Zn+])([CH3:22])([CH3:21])[CH3:20].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:14]=[CH:13][C:12]([CH2:25][C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:27])=[C:11]([O:16][CH3:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 129859234-(Benzyloxy)-1-bromo-2-methoxybenzeneHCID 178451183HCID 178451183, compound

Product 1

HCID 67304738Tert-butyl 2-(4-benzyloxy-2-methoxyphenyl)acetateYield 98.2%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(benzyloxy)-1-bromo-2-methoxybenzene (2.0 g, 6.82 mmol) in THF (20 ml) was added 2-tert-butoxy-2-oxoethylzinc chloride (27.3 ml, 13.64 mmol). Nitrogen gas bubbled through the mixture for 10 min. then Pd2(dba)3 (0.312 g, 0.341 mmol) and X-PHOS (0.325 g, 0.682 mmol) were added and the resulting mixture heated at 60° C. for 30 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 (0-50%) to afford the title compound (2.2 g, 98%). LC/MS (m/z): 351 (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-4f19ee91f67c4e97a22644771a898395
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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