Water → HCID 15205870, compound

HRID 619792Notes

Reaction equation

HRID 619792 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].C([Li])CCC.I[C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1.O>C1COCC1.CCOCC.CCOC(C)=O.[Cl-].[Cl-].[Zn+2].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1

Participants

10

Reactant 4

HCID 962WaterHCID 113582-BromoanisoleHCID 115221-Bromo-4-iodobenzeneHCID 178418339Butyllithium

Product 1

HCID 15205870HCID 15205870, compoundYield 53.5%

Reagents, catalysts & solvents 5

HCID 3007855ZincchlorideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromoanisole (3.5 g, 18.7 mmol) in 40 mL of THF at -7° C. is added n-butyl lithium (11.7 mL of a 1.6 M solution in THF, 18.7 mmol). The solution is stirred for 15 minutes. After this time, ZnCl2 (20 mL of a 1 M solution in Et2O, 20 mmol) is added. The solution is allowed to warm to ambient temperature, and stirred for 3 hours. After this time, a solution of 4-iodobromobenzene (5.6 g, 19.8 mmol) and tetrakis(triphenylphosphine)-palladium(0) (1.1 g, 1 mmol) in 30 mL of THF is added. The reaction mixture is stirred for 16 hours. After this time, the solution is poured into 100 mL of H2O. The solution is diluted with EtOAc. The organic layer is washed with 2 N NH4OH, H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered, and concentrated. The crude product is purified by column chromatography eluting with gradient of 10% CH2Cl2 /hexanes to 20% CH2Cl2 /hexanes to afford the title compound (2.61 g, 10 mmol) as a crystalline solid.

Workup

  1. stirringstirred for 3 hours
  2. stirringThe reaction mixture is stirred for 16 hours
  3. washThe organic layer is washed with 2 N NH4OH, H2O and saturated NaCl
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by column chromatography
  8. washeluting with gradient of 10% CH2Cl2 /hexanes to 20% CH2Cl2 /hexanes

Sources & evidence

ORD record
ord-38c9ec200f214e39a9c55b6eef9fb670
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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