Hydrochloric Acid → 2-Bromo-9,10-di(naphthalen-1-yl)anthracene

HRID 2167316Notes

Reaction equation

HRID 2167316 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Li][CH2:13][CH2:14][CH2:15][CH3:16].[Br:17][C:18]1[CH:31]=[CH:30][C:29]2[C:28](=O)[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21](=O)[C:20]=2[CH:19]=1.Cl>C(O)(=O)C.C1COCC1>[Br:17][C:18]1[CH:31]=[CH:30][C:29]2[C:20](=[C:21]([C:13]3[C:11]4[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:16]=[CH:15][CH:14]=3)[C:22]3[C:27]([C:28]=2[C:2]2[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:5]=[CH:4][CH:3]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 70011-BromonaphthaleneHCID 2210132-BromoanthraquinoneHCID 178418339Butyllithium

Product 1

HCID 536275472-Bromo-9,10-di(naphthalen-1-yl)anthracene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

360 g (1.74 mol) of bromonaphthalene was dissolved with THF in a 5 L flask and the temperature was lowered to −78° C. and 1600 ml (1.6 mol) of 1.6M n-BuLi was slowly added dropwise thereto. The mixture was stirred for one hour, and then 200 g (0.68 mol) of 2-bromoanthraquinone was added thereto in a solid state and then the temperature was slowly raised to room temperature and the resultant mixture was stirred. After 12 hours, 500 ml of 2N HCl(aq) was added thereto. Then, an organic layer was isolated and dried over MgSO4 and condensed under reduced pressure, thereby producing Compound C. The Compound C was used in the subsequent reaction without purification. Compound C, 346 g (2.09 mol) of KI, and 443 g (4.1 mol) of NaH2PO2.H2O were diluted with an acetic acid and then the mixture was refluxed while heating. The temperature was lowered to room temperature and thus a solid was precipitated. The solid was filtered, washed with excess water and MeOH, and re-crystallized with 300 ml of toluene, thereby producing 2-bromo-9,10-di(2-naphthyl)anthracene (230 g, 64%).

Workup

  1. customwas lowered to −78° C.
  2. waitAfter 12 hours
  3. customThen, an organic layer was isolated
  4. dry with materialdried over MgSO4 and condensed under reduced pressure
  5. customThe Compound C was used in the subsequent reaction without purification
  6. temperaturethe mixture was refluxed
  7. temperaturewhile heating
  8. customwas lowered to room temperature
  9. customthus a solid was precipitated
  10. filtrationThe solid was filtered
  11. washwashed with excess water and MeOH
  12. customre-crystallized with 300 ml of toluene

Sources & evidence

ORD record
ord-83a0102a25dd4bea855b24dbd7a3d6d6
Source dataset
uspto-grants-2015_06
Patent number
US09045419B2

Reaction notes

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