Anthraquinone → HCID 22138025, compound

HRID 901754Notes

Reaction equation

HRID 901754 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)=[CH:4][CH:3]=1.[CH2:18]([Li])[CH2:19][CH2:20][CH3:21].[CH:23]1[C:36]2[C:35](=[O:37])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28](=[O:38])[C:27]=2[CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>CCCCCC.C1COCC1.C1(C)C=CC=CC=1>[CH:18]1[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:21]=[CH:20][C:19]=1[C:8]1[CH:17]=[CH:16][C:15]([C:35]2([OH:37])[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:28]([C:2]3[CH:3]=[CH:4][C:5]([C:8]4[CH:9]=[CH:10][C:11]5[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=5)[CH:17]=4)=[CH:6][CH:7]=3)([OH:38])[C:27]3[C:36]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 6780AnthraquinoneHCID 25517Ammonium ChlorideHCID 54617522-(4-Bromophenyl)naphthaleneHCID 178418339Butyllithium

Product 1

HCID 22138025HCID 22138025, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

Under an atmosphere of argon, 2-(4-bromophenyl)naphthalene (5.4 g, 19 mmole, 2.8 eq) was dissolved into a mixed solvent composed of anhydrous toluene (25 ml) and anhydrous THF (25 ml) and the resultant solution was cooled at −40° C. in a dry ice/methanol bath. To the cooled solution, a hexane solution of n-butyllithium (1.50 mole/liter, 14 ml, 21 mmole, 1.1 eq) was added and the resultant mixture was stirred at −20° C. for 1 hour. To the resultant solution, anthraquinone (1.4 g, 6.7 mmole) was added and the obtained mixture was stirred at −20° C. for 1 hour and at the room temperature for 3 hours and left standing for one night. To the obtained reaction mixture, a saturated aqueous solution of ammonium chloride (20 ml) was added. The formed solid was separated by filtration and washed with water, methanol and acetone and a white solid (3.7 g, 91%) was obtained.

Workup

  1. waitleft
  2. waitstanding for one night
  3. customTo the obtained reaction mixture
  4. customThe formed solid was separated by filtration
  5. washwashed with water, methanol and acetone

Sources & evidence

ORD record
ord-03c10e9b858141208dc2a016fdedb8cb
Source dataset
uspto-grants-2008_04
Patent number
US07361796B2

Reaction notes

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