5-Bromo-2-iodotoluene → HCID 59715291, compound

HRID 2223322Notes

Reaction equation

HRID 2223322 reaction equation
O.[OH-].[Ba+2].[OH-].[Br:5][C:6]1[CH:11]=[CH:10][C:9](I)=[C:8]([CH3:13])[CH:7]=1.[Cl:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1>O1CCOCC1.O.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.[Pd]>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:14])[CH:20]=2)=[C:8]([CH3:13])[CH:7]=1

Participants

7

Reactant 3

HCID 27246015-Bromo-2-iodotolueneHCID 2734323(3-Chlorophenyl)boronic acidHCID 17749100Barium hydroxide, monohydrate

Product 1

HCID 59715291HCID 59715291, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Barium hydroxide monohydrate (2.27 g, 2.0 equiv), 4-bromo-1-iodo-2-methylbenzene (0.94 mL, 1.1 equiv), 3-chlorophenyl boronic acid (0.94 g, 1.0 equiv), and palladium tetrakis(triphenylphosphine) (0.14 g, 0.02 equiv) were combined and stirred in dioxane (15 mL) and water (5 mL), heated at reflux for 2 hr and then allowed to cool to room temperature. The solution was concentrated and the residue dissolved in CH2Cl2, washed with water and brine and then dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (SiO2, hexane) to give 4-bromo-3′-chloro-2-methyl biphenyl (0.33 g, 21%).

Workup

  1. temperatureat reflux for 2 hr
  2. concentrationThe solution was concentrated
  3. dissolutionthe residue dissolved in CH2Cl2
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (SiO2, hexane)

Sources & evidence

ORD record
ord-cfb2c92c54404e718eed4e571fca6e95
Source dataset
uspto-grants-2008_05
Patent number
US07375125B2

Reaction notes

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