1-Bromo-4-iodobenzene → HCID 18795255, compound

HRID 2174545Notes

Reaction equation

HRID 2174545 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.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>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]2[C:10]([OH:9])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 115221-Bromo-4-iodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 2773454(2-Hydroxyphenyl)boronic acid

Product 1

HCID 18795255HCID 18795255, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1-Bromo-4-iodobenzene (Aldrich, 2 g, 7.07 mmol), (2-hydroxyphenyl)boronic acid (Aldrich, 1.073 g, 7.78 mmol), Pd(Ph3P)4 (0.204 g, 0.177 mmol) were dissolved in 1,4-dioxane (30 mL) and water (10 mL), K3PO4 (2.251 g, 10.60 mmol) was added. The reaction mixture was stirred at 100° C. overnight. Solvents were removed under reduced pressure and DCM was added, mixture was washed with water, dried over anhydrous sodium sulfate. Then solvent was removed under reduced pressure to give the title product 4′-bromo-2-biphenylol (1.85 g, 6.54 mmol, 92% yield) as brown oil. LCMS: (M+H)+=247-249; Rt=3.52 min.

Workup

  1. customSolvents were removed under reduced pressure and DCM
  2. additionwas added
  3. washmixture was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThen solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4f620dfccc6c4915875a20f0dcb40c79
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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