Dimethylformamide → HCID 18976943, compound

HRID 2393690Notes

Reaction equation

HRID 2393690 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][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[C:5]=2[CH:4]=1.[C:28]1([P:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CN(C)C=O>C(OCC)C>[C:41]1([PH+:34]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=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][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 18976936HCID 18976936, compound

Product 1

HCID 18976943HCID 18976943, compoundYield 127.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 1 L three-hole flask equipped with a stirrer, a thermometer and a reflux condenser, 24.9 g (0.05 mol) of 2,7-bis(bromomethyl)-9-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}fluorene, 39.3 g (0.15 mol) of triphenylphosphine, and 300 ml of dimethylformamide were introduced and reacted for 12 hours at reflux temperature. After reaction, the temperature was decreased to room temperature, and the reactant was dropped down slowly in 1.5 L of ethylether solvent under agitation, to obtain a white solid. After filtering, such extracted solid was washed several times with ethylether, and then dried sufficiently in a vacuum oven at 40° C. As a result, 48.5 g (yield: 95%) of a white solid was obtained. [1H=NMR (CDCl3), δ 1.22-1.41(m, 2H, CH2), 2.16-2.42(br, s, 3H, OCH3), 3.41-3.71(m, 10H, OCH2 CH2), 4.18(t, 1H, CH), 5.58-5.81(d, 4H, CH2Br), 6.81-7.22(m, 6H, fluoreyl aromatic), 7.27-7.84(m, 30H, aromatic)].

Workup

  1. customreacted for 12 hours
  2. temperatureat reflux temperature
  3. customAfter reaction
  4. customwas decreased to room temperature
  5. customto obtain a white solid
  6. filtrationAfter filtering
  7. extractionsuch extracted solid
  8. washwas washed several times with ethylether
  9. customdried sufficiently in a vacuum oven at 40° C

Sources & evidence

ORD record
ord-f099291055fc49aca13ea07e6d9d0e6b
Source dataset
uspto-grants-1998_09
Patent number
US05807974

Reaction notes

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