Sodium Carbonate → HCID 12085900, compound

HRID 1860291Notes

Reaction equation

HRID 1860291 reaction equation
Br/[C:2](/[Si:12]([CH3:15])([CH3:14])[CH3:13])=[C:3](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)\[CH2:4][CH3:5].[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[F:16][C:17]1[CH:22]=[CH:21][C:20](/[C:2](/[Si:12]([CH3:15])([CH3:14])[CH3:13])=[C:3](/[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)\[CH2:4][CH3:5])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 13450058HCID 13450058, compound

Product 1

HCID 12085900HCID 12085900, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of (E)-1-bromo-2-phenyl-1-(trimethylsilyl)-1-butene (Miller R. B., Al-Hassam, M. I. J. Org. Chem. 1985, 50, 2121-2123) (1) (4.4 g, 15.5 mmol) in DME (50 mL) was added 4-fluorobenzene boronic acid (2.63 g, 18.9 mmol), tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.9 mmol), and 2N aqueous sodium carbonate(9.5 mL, 19 mmol). After refluxing overnight the solvent was removed under reduced pressure and the residue was chromatographed (silica gel, hexanes) to give (2) as a white solid (4.2 g, 91%): 1 H NMR (CDCl3) δ 7.30 (m, 3 H), 7.19 (m, 2 H), 7.00 (m, 4 H), 2.12 (q, J=7.7 Hz, 2 H), 0.72 (t, J=7.7 Hz, 3 H), −0.35 (s, 9 H).

Workup

  1. temperatureAfter refluxing overnight the solvent
  2. customwas removed under reduced pressure
  3. customthe residue was chromatographed (silica gel, hexanes)

Sources & evidence

ORD record
ord-6f359c53c1d54213ab23dc44f6c5f44d
Source dataset
uspto-grants-2003_03
Patent number
US06528681B2

Reaction notes

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