Hydrochloric Acid → HCID 59582968, compound

HRID 2405451Notes

Reaction equation

HRID 2405451 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>C(OCC)C.CCCCCC>[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 8058HexaneSolvent

Conditions

Temperature
-40 °C

Procedure

A flask was charged with 5.87 g of 10-bromobenzo[g]chrysene in an argon atmosphere. 100 mL of dehydrated diethyl ether was then added to the flask. After cooling the reaction solution to −40° C., 11 mL of a 1.6 M hexane solution of n-butyllithium was added to the reaction solution. The mixture was heated to 0° C., and stirred for 1 hour. After cooling the reaction solution to −60° C., a dehydrated diethyl ether (10 mL) solution of 7.72 g of triisopropyl borate was added dropwise to the reaction solution. The reaction solution was stirred at room temperature for 5 hours. After the addition of 50 mL of a 10% hydrochloric acid aqueous solution, the mixture was stirred for 1 hour. After removing the aqueous phase, the organic phase was washed with water and a saturated sodium chloride solution, and dried over magnesium sulfate. After removing magnesium sulfate by filtration, the organic phase was concentrated. The resulting solid was washed with hexane to obtain 3.18 g of the target benzo[g]chrysene-10-boronic acid (yield: 60%).

Workup

  1. temperatureThe mixture was heated to 0° C.
  2. temperatureAfter cooling the reaction solution to −60° C.
  3. stirringThe reaction solution was stirred at room temperature for 5 hours
  4. stirringthe mixture was stirred for 1 hour
  5. customAfter removing the aqueous phase
  6. washthe organic phase was washed with water
  7. dry with materiala saturated sodium chloride solution, and dried over magnesium sulfate
  8. customAfter removing magnesium sulfate
  9. filtrationby filtration
  10. concentrationthe organic phase was concentrated
  11. washThe resulting solid was washed with hexane

Sources & evidence

ORD record
ord-82679396a3ed40c1a0299472863da627
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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