Isopropyl iodide → 2-(4-Isopropoxy-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 46279Notes

Reaction equation

HRID 46279 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:17])[CH:5]=[CH:6][C:7]=1[B:8]1[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]1.[H-].[Na+].I[CH:21]([CH3:23])[CH3:22]>CN(C)C=O>[CH:21]([O:17][C:4]1[CH:5]=[CH:6][C:7]([B:8]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH3:16])([CH3:15])[O:9]2)=[C:2]([CH3:1])[CH:3]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 574432723-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 594365172-(4-Isopropoxy-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 74.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a flame-dried flask under nitrogen, 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (see WO2007092751A, 2.30 g, 9.82 mmol) was dissolved in dimethylformamide (40 mL). Sodium hydride 60% dispersion in mineral oil (0.48 g, 12 mmol) was added to the mixture. The reaction mixture was stirred at room temperature under nitrogen for 30 minutes. 2-Iodopropane (2.55 g, 15.00 mmol) was added and the reaction mixture was stirred at 70° C. for 18 hours. The reaction mixture was quenched with water. The organics were extracted 3 times with diethylether. The organic layers were combined, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography, using as eluant a mixture of heptane/ethyl acetate, to afford 2.02 g (73% yield) of 2-(4-isopropoxy-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane as a yellow oil. MS m/z 277 [MH]+

Workup

  1. stirringthe reaction mixture was stirred at 70° C. for 18 hours
  2. customThe reaction mixture was quenched with water
  3. extractionThe organics were extracted 3 times with diethylether
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. additiona mixture of heptane/ethyl acetate

Sources & evidence

ORD record
ord-1d448f14ae0146519a9ff661d48ca468
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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