Water → 9,9-Di(9,9-dihexylfluoren-2-yl)-2,7-dibromofluorene

HRID 1434497Notes

Reaction equation

HRID 1434497 reaction equation
[CH2:1]([C:7]1([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CS(O)(=O)=O.O.[CH2:32]([C:38]1([CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])[C:50]2[CH:49]=[C:48]([C:51]3(O)[C:63]4[CH:62]=[C:61]([Br:64])[CH:60]=[CH:59][C:58]=4[C:57]4[C:52]3=[CH:53][C:54]([Br:65])=[CH:55][CH:56]=4)[CH:47]=[CH:46][C:45]=2[C:44]2[C:39]1=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>ClCCl>[CH2:20]([C:7]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:19]2[CH:18]=[C:17]([C:51]3([C:48]4[CH:47]=[CH:46][C:45]5[C:44]6[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=6)[C:38]([CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:50]=5[CH:49]=4)[C:63]4[CH:62]=[C:61]([Br:64])[CH:60]=[CH:59][C:58]=4[C:57]4[C:52]3=[CH:53][C:54]([Br:65])=[CH:55][CH:56]=4)[CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 51284499,9-dihexylfluoreneHCID 68800602HCID 68800602, compound

Product 1

HCID 860624429,9-Di(9,9-dihexylfluoren-2-yl)-2,7-dibromofluorene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 2 L round-bottom flask, 50 g of the compound (1) and 200 g of 9,9-dihexylfluorene were dissolved in 1000 ml of dichloromethane, and then the temperature was decreased to 0° C. The reaction solution was slowly added with a s olution of 10 ml of methane sulfonic acid dissolved in 100 ml of dichloromethane with stirring, followed by further stirring for 2 hours. The resulting reaction solution was poured into water, after which an extraction was performed using diethyl ether. The solvent was evaporated using a rotary evaporator. A column chromatography separation resulted in 60 g (58%) of (9,9-di(9,9-dihexylfluoren-2-yl)-2,7-dibromofluorene) (2).

Workup

  1. customwas decreased to 0° C
  2. additionThe reaction solution was slowly added with
  3. stirringby further stirring for 2 hours
  4. customThe resulting reaction solution
  5. extractionafter which an extraction
  6. customThe solvent was evaporated
  7. customa rotary evaporator
  8. customA column chromatography separation
  9. customresulted in 60 g (58%) of (9,9-di(9,9-dihexylfluoren-2-yl)-2,7-dibromofluorene) (2)

Sources & evidence

ORD record
ord-579c6a6109f340f59f538c763a74a944
Source dataset
uspto-grants-2009_11
Patent number
US07615289B2

Reaction notes

Loading…