Dimethylformamide → HCID 86753116, compound

HRID 2393688Notes

Reaction equation

HRID 2393688 reaction equation
[Br:1][CH2:2][C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([CH2:16][Br:17])=[CH:10][CH:11]=3)[CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:5]=2[CH:4]=1.[C:24]1([P:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CN(C)C=O>C(OCC)C>[C:37]1([PH+:30]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1.[Br:1][CH2:2][C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([CH2:16][Br:17])=[CH:10][CH:11]=3)[CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 67672649HCID 67672649, compound

Product 1

HCID 86753116HCID 86753116, compoundYield 131.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 1 L three-neck flask equipped with a stirrer, a thermometer and a reflux condenser, 43.6 g (0.1 mol) of 2,7-bis(bromomethyl)-9-normal-hexylfluorene, 78.7 g (0.3 mol) of triphenylphosphine, and 500 ml of dimethylformamide were introduced and reacted for 12 hours at reflux temperature. When the temperature was decreased to room temperature after reaction, and the reaction solution was dropped down slowly into a 3 L ethylether solvent being thoroughly stirred, to obtain a white solid. After filtering, this solid was washed several times with ethylether, and then dried sufficiently in a vacuum oven at a temperature of 40° C. As a result, 92.2 g (yield: 96%) of a white solid was obtained. [1H-NMR (CDCl3), δ 0.25(br, 3H, CH3), 1.60-1.24(m, 10H, CH2), 2.83(t, 1H, CH), 5.66-5.76(d, 4H, CH2Br), 6.76-7.11(m, 6H, aromatic fluorenyl), 7.49-7.81(m, 30H, aromatic)].

Workup

  1. customIn a 1 L three-neck flask equipped with a stirrer
  2. customreacted for 12 hours
  3. temperatureat reflux temperature
  4. customwas decreased to room temperature
  5. customafter reaction
  6. customto obtain a white solid
  7. filtrationAfter filtering
  8. washthis solid was washed several times with ethylether
  9. customdried sufficiently in a vacuum oven at a temperature of 40° C

Sources & evidence

ORD record
ord-b0379311a0c447debd67d75392e2ba0a
Source dataset
uspto-grants-1998_09
Patent number
US05807974

Reaction notes

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