Water → HCID 67148379, compound

HRID 2428114Notes

Reaction equation

HRID 2428114 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH:16]=1)[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C([O-])([O-])=O.[K+].[K+].O.[CH3:25][C:26]1(C)C(C)(C)OB(C=C)O1>COCCOC.CCOCC.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>[C:12]([Si:9]([O:8][CH2:7][C:6]1[CH:16]=[C:2]([CH:25]=[CH2:26])[CH:3]=[CH:4][C:5]=1[Cl:17])([CH3:11])[CH3:10])([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 58007486HCID 58007486, compound

Product 1

HCID 67148379HCID 67148379, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Pd(PPh3)4 (173 mg, 0.149 mmol) was added to a sol. of (5-bromo-2-chloro-benzyloxy)-tert-butyl-dimethyl-silane (1.00 g, 2.98 mmol) in DME (30 mL). The mixture was stirred at rt for 20 min, and K2CO3 (411 mg, 2.98 mmol), water (10 mL) and 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.53 mL, 2.98 mmol) were added. The mixture was heated rapidly to reflux, and stirred under reflux for 2 h. The mixture was allowed to cool to rt, and was diluted with Et2O (100 mL). The mixture was washed with water, and the aq. layer was extracted back with Et2O (3×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 5:95) yielded the title compound (822 mg, 98%). LC-MS: tR=1.22 min.

Workup

  1. temperatureThe mixture was heated rapidly
  2. temperatureto reflux
  3. stirringstirred
  4. temperatureunder reflux for 2 h
  5. temperatureto cool to rt
  6. washThe mixture was washed with water
  7. extractionthe aq. layer was extracted back with Et2O (3×)
  8. dry with materialextracts were dried over MgSO4
  9. filtrationfiltered
  10. customthe solvents were removed under reduced pressure
  11. customPurification of the crude by FC (EtOAc/heptane 5:95)

Sources & evidence

ORD record
ord-f74d1c14ed724520b6b141c9be7da140
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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