Hydrochloric Acid → HCID 58113574, compound

HRID 2421755Notes

Reaction equation

HRID 2421755 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:48]3[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=3)[C:21]3[CH:20]=[C:19]([N:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:18]=[CH:17][C:16]=3[C:15]3[C:10]2=[CH:11][C:12]([N:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:13][CH:14]=3)=[CH:5][CH:4]=1.B(Br)(Br)Br.Cl>ClCCl>[CH:15]([C:16]1[CH:17]=[CH:18][C:19]([CH2:1][O:2][C:3]2[CH:4]=[CH:5][C:6]([C:9]3([C:48]4[CH:49]=[CH:50][C:51]([O:54][CH2:55][C:3]5[CH:4]=[CH:5][C:6]([CH:9]=[CH2:10])=[CH:7][CH:8]=5)=[CH:52][CH:53]=4)[C:10]4[CH:11]=[C:12]([N:35]([C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=5)[C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[CH:13]=[CH:14][C:15]=4[C:16]4[C:21]3=[CH:20][C:19]([N:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=4)=[CH:7][CH:8]=2)=[CH:20][CH:21]=1)=[CH2:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromide2×HCID 57535851HCID 57535851, compound2×

Product 1

HCID 58113574HCID 58113574, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5.36 g (7.52 mmol) of 9,9-di(4-methoxyphenyl)-2,7-bis(diphenylamino)fluorene (Compound 2) is dissolved in 25 ml of dichloromethane and the solution cooled in a dry ice-acetone bath under the protection of flowing nitrogen. To this solution, 34 ml (34 mmol) of a 1.0 M solution of boron tribromide in dichloromethane is added dropwise while the reaction is stirred. After the addition of boron tribromide, the reaction mixture is allowed to warm to room temperature and is stirred at room temperature overnight. The reaction mixture is then poured into 300 g of crushed ice. Concentrated HCl (1.0 ml) is added and the aqueous mixture stirred at room temperature for 2 h. The mixture is then extracted with dichloromethane and the combined organic layer is dried over anhydrous magnesium sulfate. The solution is filtered and the solvent removed on a rotary evaporator. The crude product is re-dissolved in a small amount of ethyl acetate and purified on a silica gel column eluted by a mixture of ethyl acetate and hexane (9:1 v/v). After the solvent is removed, the solid is re-crystallized from the mixed solvent of ethanol and ethyl acetate to give 3.5 g of the final product as off-white crystals. Purity: 96.7 percent (HPLC)

Workup

  1. temperaturethe solution cooled in a dry ice-acetone bath under the protection of flowing nitrogen
  2. stirringis stirred at room temperature overnight
  3. stirringthe aqueous mixture stirred at room temperature for 2 h
  4. extractionThe mixture is then extracted with dichloromethane
  5. dry with materialthe combined organic layer is dried over anhydrous magnesium sulfate
  6. filtrationThe solution is filtered
  7. customthe solvent removed on a rotary evaporator
  8. dissolutionThe crude product is re-dissolved in a small amount of ethyl acetate
  9. custompurified on a silica gel column
  10. washeluted by a mixture of ethyl acetate and hexane (9:1 v/v)
  11. customAfter the solvent is removed
  12. customthe solid is re-crystallized from the mixed solvent of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-3ecf22fcbb1546a08ee3aa843cbeb129
Source dataset
uspto-grants-2011_06
Patent number
US07956350B2

Reaction notes

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