Triisopropyl borate → HCID 59439581, compound

HRID 71053Notes

Reaction equation

HRID 71053 reaction equation
I[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[C:4]([CH3:12])[C:3]=1[I:13].C([Mg]Cl)(C)C.[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C.[NH4+].[Cl-]>CCOCC.C1COCC1>[I:13][C:3]1[C:4]([CH3:12])=[C:5]([O:10][CH3:11])[C:6]([O:8][CH3:9])=[CH:7][C:2]=1[B:19]([OH:24])[OH:20]

Participants

7

Reactant 4

HCID 21531Triisopropyl borateHCID 25517Ammonium ChlorideHCID 59439582HCID 59439582, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 59439581HCID 59439581, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,2-diiodo-4,5-dimethoxy-3-methylbenzene (Example 5(b), 2.0 g, 4.95 mmol) in 120 mL of a mixture of THF and Et2O (1:1) was added dropwise at −78° C., isopropylmagnesium chloride (2 M in THF, 2.72 mL, 5.44 mmol). After the mixture was stirred for 2 h at that temperature, B(OiPr)3 (10.50 ml, 14.84 mmol) was added. The solution was warmed to room temperature overnight; then a saturated solution of NH4Cl 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), dried over Na2SO4 and concentrated. To the concentrated sample, hexane was added and the resulting precipitate was isolated to give 0.90 g of the pure product (56%).

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted with Et2O (50 mL, 3 times)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. additionTo the concentrated sample, hexane was added
  6. customthe resulting precipitate was isolated

Sources & evidence

ORD record
ord-450a6a6d07304294b12c5a36314c2901
Source dataset
uspto-grants-2014_09
Patent number
US08822720B2

Reaction notes

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