Hydrochloric Acid → HCID 59582968, compound

HRID 889784Notes

Reaction equation

HRID 889784 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.CCO[CH2:27][CH3:28].CCCCCC.C([Li])CCC.Cl.[B:41](OC(C)C)([O:46]C(C)C)[O:42]C(C)C>>[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:28][C:27]([B:41]([OH:46])[OH:42])=[C:14]1[C:19]=3[CH:18]=[CH:17][CH:16]=[CH:15]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 21531Triisopropyl borateHCID 14415981HCID 14415981, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 59582968HCID 59582968, compoundYield 60%

Conditions

Temperature
-40 °C

Procedure

Under an argon atmosphere, 5.87 g of 10-bromobenzo[g]chrysene which had been prepared in Synthesis Example 2 was placed in a flask and 100 mL of dehydrated ether was added to this flask. The reaction solution was cooled to −40° C. and 11 ml of 1.6M n-butyllithium hexane solution was added. After heating to 0° C., the resultant was stirred for 1 hour. The reaction solution was cooled to −60° C. and 10 mL of dehydrated ether solution in which 7.72 g of triisopropyl borate was dissolved was added. The reaction solution was stirred for 5 hours with heating to room temperature. 50 mL of 10% aqueous solution of hydrochloric acid was added and stirring was conducted for 1 hour. An aqueous phase was removed and an organic phase which had been separated 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 benzo[g]chrysene-10-boronic acid was obtained.

Workup

  1. customwas placed in a flask
  2. temperatureAfter heating to 0° C.
  3. temperatureThe reaction solution was cooled to −60° C.
  4. additionwas added
  5. stirringThe reaction solution was stirred for 5 hours
  6. temperaturewith heating to room temperature
  7. stirringstirring
  8. waitwas conducted for 1 hour
  9. customAn aqueous phase was removed
  10. customan organic phase which had been separated
  11. washwas washed with water and saturated brine
  12. dry with materialdried with magnesium sulfate
  13. filtrationAfter the magnesium sulfate was filtered out
  14. concentrationthe organic phase was concentrated
  15. washThe resulting solids were washed with hexane

Sources & evidence

ORD record
ord-8b4ba2cd6f0f411f8ae6c96eb7c21df9
Source dataset
uspto-grants-2012_08
Patent number
US08253129B2

Reaction notes

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