Water → HCID 58836110, compound

HRID 600155Notes

Reaction equation

HRID 600155 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[Li]CCCC.C(O[B:32]1[O:36][C:35]([CH3:38])([CH3:37])[C:34]([CH3:40])([CH3:39])[O:33]1)(C)C.O>C1COCC1>[CH3:39][C:34]1([CH3:40])[C:35]([CH3:38])([CH3:37])[O:36][B:32]([C:2]2[C:3]3[C:8]([C:9]([C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=4)=[C:10]4[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)[O:33]1

Participants

6

Reactant 4

HCID 962WaterHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 14934743HCID 14934743, compoundHCID 178418339Butyllithium

Product 1

HCID 58836110HCID 58836110, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4.6 g (1 eq, 13.25 mmol) of 9-bromo-10-p-tolyl-anthracene was dissolved in 150 ml of THF in a 500 ml round-bottomed flask in Ar gas condition, and 6.36 ml (1.2 eq, 15.9 mmol) of 2.5M n-BuLi (in hexane) was added to the solution at −78° C. After stirring the solution at −78° C. for 1 hour, 3.52 ml (1.3 eq, 17.23 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added to the solution and stirred at room temperature for 2 hours. Next, 50 ml of water was added to the solution to terminate the reaction, and the organic phase of the solution was extracted using brine and methylene chloride. The extracted organic phase was dried using anhydrous magnesium sulfate and filtered to remove the solvent. The dried organic phase was dissolved in a small amount of toluene and subjected to column chromatography (silica and hexane) to remove impurities. Next, the polarity of the eluent solvent was increased to obtain 3.5 g (67%) of a white solid.

Workup

  1. additionwas added to the solution at −78° C
  2. stirringstirred at room temperature for 2 hours
  3. customto terminate
  4. customthe reaction
  5. extractionthe organic phase of the solution was extracted
  6. customThe extracted organic phase was dried
  7. filtrationfiltered
  8. customto remove the solvent
  9. dissolutionThe dried organic phase was dissolved in a small amount of toluene
  10. customto remove impurities
  11. temperatureNext, the polarity of the eluent solvent was increased

Sources & evidence

ORD record
ord-f4db59bbd2d0419f81a89a2b3bf28b4f
Source dataset
uspto-grants-2011_03
Patent number
US07901793B2

Reaction notes

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