Hydrochloric Acid → HCID 59622694, compound

HRID 1890212Notes

Reaction equation

HRID 1890212 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[C:12]4[C:13]5C=CC=C[C:14]=5[CH:15]=[CH:16][C:17]=4[CH:18]=[CH:19][C:20]=3[CH:21]=2)=[CH:4][CH:3]=1.[CH2:26]([Li])[CH2:27][CH2:28][CH3:29].[B:31](OC(C)C)([O:36]C(C)C)[O:32]C(C)C.Cl>CCOCC.CCCCCC>[CH:26]1[C:20]2[C:19]3[C:14]4[CH:13]=[CH:12][CH:11]=[CH:10][C:15]=4[CH:16]=[CH:17][C:18]=3[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([B:31]([OH:36])[OH:32])=[CH:3][CH:4]=3)[C:21]=2[CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 86649137HCID 86649137, compoundHCID 178418339Butyllithium

Product 1

HCID 59622694HCID 59622694, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-40 °C

Procedure

Under an argon atmosphere, 7.66 g of 10-(4-bromophenyl)benzo[c]phenanthrene was placed in a flask. 400 mL of dehydrated ether was added to the flask. The reaction solution was cooled to −40° C. Then 14 mL of a 1.6M hexane solution of n-butyllithium was added. After heating to 0° C., the solution was stirred for an hour. The reaction solution was cooled to −60° C. Then, 20 mL of a dehydrated ether solution in which 9.41 g of triisopropyl borate was solved was dripped. The reaction solution was stirred for five hours while heating to room temperature. 100 mL of a 10% hydrochloric acid solution was added and further 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 resulting solids were washed with hexane, whereby 4.18 g (yield: 60%) of 4-[benzo[c]phenanthrene-5-yl]phenylboronic acid was obtained.

Workup

  1. temperatureAfter heating to 0° C.
  2. temperatureThe reaction solution was cooled to −60° C
  3. stirringThe reaction solution was stirred for five hours
  4. temperaturewhile heating to room temperature
  5. stirringfurther stirred for an hour
  6. customAn aqueous phase was removed
  7. customan organic phase which had been separated
  8. washwas washed with water and saturated brine
  9. dry with materialdried with magnesium sulfate
  10. filtrationAfter the magnesium sulfate was filtered out
  11. concentrationthe organic phase was concentrated
  12. washThe resulting solids were washed with hexane

Sources & evidence

ORD record
ord-39543741a2e5432b8e30f2f5c80d969d
Source dataset
uspto-grants-2013_08
Patent number
US08507106B2

Reaction notes

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