Hydrochloric Acid → HCID 16732350, compound

HRID 1170772Notes

Reaction equation

HRID 1170772 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].[B:12]([O:17]C)(OC)[O:13]C.Cl.[CH2:20]1[CH2:24]O[CH2:22][CH2:21]1>C1(C)C=CC=CC=1>[CH:3]1[C:2]2[C:7]3[C:8](=[C:22]([B:12]([OH:17])[OH:13])[C:21]4[CH:1]=[CH:2][CH:3]=[CH:4][C:20]=4[CH:24]=3)[CH:9]=[CH:10][C:1]=2[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8058HexaneHCID 8470Trimethyl borateHCID 178418339Butyllithium

Product 1

HCID 16732350HCID 16732350, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-62 °C

Procedure

Into 200 ml of dehydrated THF, tetrahydrofuran, 20 g of 7-bromobenzanthracene obtained above was dissolved, and the obtained solution was cooled at −62° C. To the cooled solution, 50 ml of a 1.6 M hexane solution of normal-butyllithium was added dropwise, and the resultant mixture was stirred for 30 minutes. The temperature was raised to −5° C. and then lowered to −64° C. To the cooled fluid, a THF solution of 22.4 g of trimethyl borate was added dropwise. After one night, the reaction fluid was adjusted at the acidic condition with a dilute hydrochloric acid, treated by extraction with toluene and washed with water and a saturated aqueous solution of sodium chloride, and the organic layer was dried with anhydrous sodium sulfate. After the solvent was removed by distillation, the obtained residue was crystallized from toluene/hexane, and 14 g of 7-benzanthraceneboronic acid was obtained as cream crystals (the yield: 79%).

Workup

  1. dissolutionabove was dissolved
  2. temperatureThe temperature was raised to −5° C.
  3. customlowered to −64° C
  4. waitAfter one night
  5. washwashed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, and the organic layer was dried with anhydrous sodium sulfate
  7. customAfter the solvent was removed by distillation
  8. customthe obtained residue was crystallized from toluene/hexane

Sources & evidence

ORD record
ord-db1013e5980a4718945b1a97b980a1a3
Source dataset
uspto-grants-2010_11
Patent number
US07829206B2

Reaction notes

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