Hydrochloric Acid → 9-Anthraceneboronic Acid

HRID 646646

Reaction equation

HRID 646646 reaction equation
[Li]C(CC)C.Br[C:7]1[C:8]2[C:13]([CH:14]=[C:15]3[C:20]=1[CH:19]=[CH:18][CH:17]=[CH:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2.C([O:24][B:25](OC(C)C)[O:26]C(C)C)(C)C.Cl>CCOCC.CO>[CH:19]1[C:20]2[C:15](=[CH:14][C:13]3[C:8]([C:7]=2[B:25]([OH:26])[OH:24])=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 740629-BromoanthraceneHCID 178418400CID 53628100

Product 1

HCID 155102139-Anthraceneboronic AcidYield 94.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

sec-BuLi (4.3 mL, 6.0 mmol, 1.4M solution in cyclohexane) was added dropwise to a solution of 9-bromoanthracene (1.29 g, 5.0 mmol) in Et2O (20 mL) at 0° C. under N2. The reaction was held at 0° C. for 15 minutes then warmed to rt and stirred an additional 45 minutes. Triisopropylborate (1.5 mL, 6.5 mmol) was added and the reaction was stirred at rt for 18 h. Concentrated HCl (1.0 mL) and MeOH (1.0 mL) was added and the reaction was stirred for 30 minutes. The layers were separated and the aqueous phase was extracted three times with CH2Cl2. The combined organic layers were washed with H2O, sat. NaHCO3 (aq.), brine, and then dried over Na2SO4. Filtration and concentration gave 1.05 g of 9-anthraceneboronic acid.

Workup

  1. stirringthe reaction was stirred at rt for 18 h
  2. stirringthe reaction was stirred for 30 minutes
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted three times with CH2Cl2
  5. washThe combined organic layers were washed with H2O, sat. NaHCO3 (aq.), brine
  6. dry with materialdried over Na2SO4
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-76ed8c58e15e49f0905b210d980324c6
Source dataset
uspto-grants-2010_04
Patent number
US07705157B2

Linked notes

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