Triisopropyl borate → HCID 59582968, compound

HRID 1515575Notes

Reaction equation

HRID 1515575 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]3)[C:12]1[CH:20]=[CH:21][CH:22]=[CH:23][C:11]=1C1[C:5]2=[CH:6][CH:7]=[CH:8]C=1.C([Li])C[CH2:26][CH3:27].[B:29](OC(C)C)([O:34]C(C)C)[O:30]C(C)C>CCOCC.CCCCCC.C1(C)C=CC=CC=1>[CH:21]1[C:20]2[C:2]3[C:3]([C:4]4[C:13]([C:12]=2[CH:11]=[CH:23][CH:22]=1)=[CH:8][CH:7]=[CH:6][CH:5]=4)=[CH:27][C:26]([B:29]([OH:34])[OH:30])=[C:14]1[C:19]=3[CH:18]=[CH:17][CH:16]=[CH:15]1

Participants

7

Reactant 3

HCID 21531Triisopropyl borateHCID 14415981HCID 14415981, compoundHCID 178418339Butyllithium

Product 1

HCID 59582968HCID 59582968, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-40 °C

Procedure

Under an atmosphere of argon, 5.87 g of 10-bromobenzo[g]chrysene was placed in a flask. Then, 200 mL of dehydrated ether and 200 mL of dehydrated toluene were added. After cooling the reaction solution to −40° C., 11 mL of a 1.6M hexane solution of n-butyl lithium was added, and the temperature was elevated to 0° C., followed by stirring for 1 hour. After cooling the reaction solution to −60° C., 10 mL of a dehydrated ether solution of 7.72 g of triisopropyl borate was added dropwisely. The stirring was conducted for 5 hours while heating the reaction solution to room temperature. Then, 100 ml of an aqueous 10% hydrochloric solution was added, followed by stirring for 1 hour. An aqueous phase was removed and an organic phase was washed with water and saturated brine, and then dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting solids were washed with hexane, whereby 3.18 g (yield: 60%) of intended benzo[g]chrysene-10-boronic acid was obtained.

Workup

  1. customwas elevated to 0° C.
  2. temperatureAfter cooling the reaction solution to −60° C.
  3. waitThe stirring was conducted for 5 hours
  4. temperaturewhile heating the reaction solution to room temperature
  5. stirringby stirring for 1 hour
  6. customAn aqueous phase was removed
  7. washan organic phase was washed with water and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. filtrationAfter the magnesium sulfate was filtered out
  10. concentrationthe organic phase was concentrated
  11. washThe resulting solids were washed with hexane

Sources & evidence

ORD record
ord-22b763dfba7e4990b4f20dbb22adde45
Source dataset
uspto-grants-2012_07
Patent number
US08222637B2

Reaction notes

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