Hydrochloric Acid → HCID 59582968, compound

HRID 2274130Notes

Reaction equation

HRID 2274130 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.Cl>CCCCCC.CCOCC>[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 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 14415981HCID 14415981, compoundHCID 178418339Butyllithium

Product 1

HCID 59582968HCID 59582968, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

Under the atmosphere of argon, 5.87 g of 10-bromobenzo[g]chrysene was placed in a flask, and 100 mL of dehydrated ether was added. After cooling the reaction solution to −40° C., 11 mL of a 1.6M hexane solution of n-butyllithium was added. The resulting solution was heated to 0° C., followed by stirring for 1 hour. The reaction solution was cooled to −60° C., and 10 mL of a dehydrated ether solution of 7.72 g of triisopropyl borate was added dropwise. The reaction solution was stirred for 5 hours while heating to room temperature. 50 mL of a 10% aqueous hydrochloric acid solution was added, followed by stirring for 1 hour. After removing an aqueous phase, and an organic phase was washed with water and saturated saline, and dried with magnesium sulfate. After filtering off magnesium sulfate, 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 as an intended product was obtained.

Workup

  1. temperatureThe resulting solution was heated to 0° C.
  2. temperatureThe reaction solution was cooled to −60° C.
  3. stirringThe reaction solution was stirred for 5 hours
  4. temperaturewhile heating to room temperature
  5. stirringby stirring for 1 hour
  6. customAfter removing an aqueous phase
  7. washan organic phase was washed with water and saturated saline
  8. dry with materialdried with magnesium sulfate
  9. filtrationAfter filtering off magnesium sulfate
  10. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-d5e8c689d5074f0cbf1d650881a8a65c
Source dataset
uspto-grants-2015_09
Patent number
US09126943B2

Reaction notes

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