Hydrochloric Acid → 2-Iodophenylboronic acid

HRID 71050Notes

Reaction equation

HRID 71050 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.C([Mg]Cl)(C)C.[B:14](OC(C)C)([O:19]C(C)C)[O:15]C(C)C.Cl>C(OCC)C.C1COCC1>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[B:14]([OH:19])[OH:15]

Participants

7

Procedure

To a solution of 1,2-diiodobenzene (0.102 g, 3.08 mmol) in 60 mL of a mixture of THF and diethylether (Et2O) (1:1) was added dropwise at −78° C. isopropylmagnesium chloride (2 M in THF, 1.54 mL, 3.08 mmol). After the mixture was stirred for 2 h at that temperature, B(OiPr)3 (1.74 g 2.12 mL, 9.24 mmol) was added. The solution was warmed to room temperature overnight; then 40 mL of HCl (10%) was added, and the resulting mixture was stirred for 30 min at room temperature. The aqueous layer was extracted with Et2O (50 mL, 3 times). Drying over Na2SO4, evaporation and purification by flash chromatography gave 0.62 g of the pure product (82%).

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted with Et2O (50 mL, 3 times)
  3. dry with materialDrying over Na2SO4, evaporation and purification by flash chromatography

Sources & evidence

ORD record
ord-06f6e3eb840544e48bc8bcd875cb7ab5
Source dataset
uspto-grants-2014_09
Patent number
US08822720B2

Reaction notes

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