Hydrochloric Acid → Benzo[c]phenanthren-5-ylboronic acid

HRID 1890209Notes

Reaction equation

HRID 1890209 reaction equation
Br[C:2]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[CH:6]=[CH:5][C:4]=2[CH:3]=1.C([Li])CCC.[B:25](OC(C)C)([O:30]C(C)C)[O:26]C(C)C.Cl>CCOCC.CCCCCC>[CH:19]1[C:14]2[C:13]3[C:12]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[CH:6]=[CH:5][C:4]=3[CH:3]=[C:2]([B:25]([OH:30])[OH:26])[C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 106624825-Bromobenzo[c]phenanthreneHCID 178418339Butyllithium

Product 1

HCID 59622711Benzo[c]phenanthren-5-ylboronic acidYield 60%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-40 °C

Procedure

Under an argon atmosphere, 10.1 g of 5-bromobenzo[c]phenanthrene which had been prepared in Synthesis Example 1 was placed in a flask. 400 mL of dehydrated ether was added to this flask. The reaction solution was cooled to −40° C., and 22 ml of 1.6M hexane solution of n-butyllithium was added. The resultant was heated to 0° C., and stirred for an hour. The reaction solution was cooled to −60° C., and 10 mL of a dehydrated ether solution of 14.4 g of triisopropyl borate was dripped. The reaction solution was stirred for 5 hours while heating to room temperature. 100 mL of a 10% hydrochloric acid solution was added and the mixture was stirred for an 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 solids obtained were washed with hexane, whereby 5.37 g (yield: 60%) of benzo[c]phenanthrene-5-boronic acid was obtained.

Workup

  1. customwas placed in a flask
  2. temperatureThe resultant was heated to 0° C.
  3. temperatureThe reaction solution was cooled to −60° C.
  4. stirringThe reaction solution was stirred for 5 hours
  5. temperaturewhile heating to room temperature
  6. stirringthe mixture was stirred for an hour
  7. customAn aqueous phase was removed
  8. customan organic phase which had been separated
  9. washwas washed with water and saturated brine
  10. dry with materialdried with magnesium sulfate
  11. filtrationAfter the magnesium sulfate was filtered out
  12. concentrationthe organic phase was concentrated
  13. customThe solids obtained
  14. washwere washed with hexane

Sources & evidence

ORD record
ord-2a4905ad09a54e1b91b97e1ebe56f6de
Source dataset
uspto-grants-2013_08
Patent number
US08507106B2

Reaction notes

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